N-(Tetrazol-5-yl)- and N-(triazol-5-yl)arylcarboxamide derivatives with herbicidal action

ABSTRACT

N-(Tetrazol-5-yl)- and N-(triazol-5-yl)arylcarboxamide derivatives of the general formula (I) are described as herbicides. 
     
       
         
         
             
             
         
       
     
     In this formula (I), V, X and Z represent radicals such as hydrogen, organic radicals such as alkyl, and other radicals such as halogen. A represents a tetrazole or triazole radical. W is CY or N.

The invention relates to the technical field of the herbicides,especially that of the herbicides for selective control of weeds andweed grasses in crops of useful plants.

N-(tetrazol-5-yl)- and N-(triazol-5-yl)arylcarboxamides are known asherbicides from WO 2012/028579 A1. WO 2013/087577 A1 discloses also asherbicides N-(tetrazol-5-yl)- and N-(triazol-5-yl)arylcarboxamidessubstituted on the amide nitrogen. Herbicidally active triazinonecarboxamides substituted on the amide nitrogen are known from WO2014/126070 A1.

It was an object of the present invention to provide herbicidally activecompounds having properties improved over those of the compoundsdisclosed in the prior art.

It has now been found that certain N-(tetrazol-5-yl)- andN-(triazol-5-yl)arylcarboxamide derivatives, which have been substitutedby specific radicals on the tetrazolyl or triazolyl radical or on thecarbamoyl group, are particularly well suited as herbicides.

Accordingly, the present invention relates to N-(tetrazol-5-yl)- andN-(triazol-5-yl)arylcarboxamide derivatives of the formula (I)

where the symbols and indices are each defined as follows:

W is N or CY,

X and Z are each independently hydrogen, nitro, halogen, cyano, formyl,thiocyanato, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl,(C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-haloalkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-halocycloalkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, (C₃-C₆)-halocycloalkyl-(C₁-C₆)-alkyl,COR¹, OR¹, OCOR¹, OSO₂R², S(O)_(n)R², SO₂OR¹, SO₂N(R¹)₂, NR¹SO₂R²,NR¹COR¹, (C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹,(C₁-C₆)-alkyl-OCOR¹, (C₁-C₆)-alkyl-OSO₂R², (C₁-C₆)-alkyl-CO₂R¹,(C₁-C₆)-alkyl-SO₂OR¹, (C₁-C₆)-alkyl-CON(R¹)₂, (C₁-C₆)-alkyl-SO₂N(R¹)₂,(C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R², NR¹R², P(O)(OR⁵)₂, orheteroaryl, heterocyclyl or phenyl, each substituted by s radicals fromthe group of methyl, ethyl, methoxy, nitro, trifluoromethyl and halogen,

Y is hydrogen, nitro, halogen, cyano, thiocyanato, (C₁-C₆)-alkyl,halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl,(C₂-C₆)-alkynyl, halo-(C₂-C₆)-alkynyl, (C₃-C₆)cycloalkyl,(C₃-C₆)-cycloalkenyl, halo-(C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,COR¹, CO₂R¹, OCO₂R¹, NR¹CO₂R¹, C(O)N(R¹)₂, NR¹C(O)N(R¹)₂, OC(O)N(R¹)₂,C(O)N(R¹)OR¹, NR¹SO₂R², NR¹COR¹, OR¹, OSO₂R², S(O)_(n)R², SO₂OR¹,SO₂N(R¹)₂, (C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹,(C₁-C₆)-alkyl-OCOR¹, (C₁-C₆)-alkyl-OSO₂R², (C₁-C₆)-alkyl-CO₂R¹,(C₁-C₆)-alkyl-CN, (C₁-C₆)-alkyl-SO₂OR¹, (C₁-C₆)-alkyl-CON(R¹)₂,(C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R²,N(R¹)₂, P(O)(OR⁵)₂, CH₂P(O)(OR⁵)₂, CH═NOR¹, (C₁-C₆)-alkyl-CH═NOR¹,(C₁-C₆)-alkyl-O—N═C(R¹)₂, (C₁-C₆)-alkylphenyl, (C₁-C₆)-alkylheteroaryl,(C₁-C₆)-alkylheterocyclyl, phenyl, heteroaryl or heterocyclyl, where thelatter 6 radicals are each substituted by s radicals from the groupconsisting of halogen, nitro, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl, S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy,halo-(C₁-C₆)-alkoxy, (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl and cyanomethyl, andwhere heterocyclyl bears n oxo groups, or

Y and Z together with the two atoms to which they are bonded form a 5-,6- or 7-membered, unsaturated, partly saturated or saturated ring which,as well as carbon atoms, in each case has s nitrogen atoms, n oxygenatoms, n sulfur atoms and n S(O), S(O)₂, C═N—R¹⁰, C(OR¹¹)₂,C[—O—(CH₂)₂—O—] or C(O) elements as ring members, wherein the carbonatoms are substituted by s radicals from the group consisting ofhalogen, cyano, (C₁-C₆)-alkyl, (C₂-C₁₀)-alkenyl, (C₂-C₁₀)-alkynyl,(C₁-C₆)-haloalkyl, (C₁-C₆)-alkoxy, phenoxy, halo-(C₁-C₆)-alkoxy,(C₃-C₈)-cycloalkyl, (C₂-C₈)-alkoxyalkyl and phenyl,

wherein the nitrogen atoms are substituted by n radicals from the groupconsisting of (C₁-C₆)-alkyl and phenyl,

and in which the aforementioned phenyl radicals are substituted by sradicals from the group consisting of cyano, nitro, halogen,(C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl and (C₁-C₆)-alkoxy,

V is hydrogen, nitro, halogen, cyano, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,OR¹ or S(O)_(n)R²,

R¹ is hydrogen, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl,(C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl, (C₃-C₆)-halocycloalkyl,(C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, phenyl,phenyl-(C₁-C₆)-alkyl, heteroaryl, (C₁-C₆)-alkylheteroaryl, heterocyclyl,(C₁-C₆)alkylheterocyclyl, (C₁-C₆)-alkyl-O-heteroaryl,(C₁-C₆)-alkyl-O-heterocyclyl, (C₁-C₆)-alkyl-NR³-heteroaryl or(C₁-C₆)-alkyl-NR³-heterocyclyl, where the 21 latter radicals aresubstituted by s radicals from the group consisting of cyano, halogen,nitro, thiocyanato, OR³, S(O)_(n)R⁴, N(R³)₂, NR³OR³, COR³, OCOR³, SCOR⁴,NR³COR³, NR³SO₂R⁴, CO₂R³, COSR⁴, CON(R³)₂ and(C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and where heterocyclyl bears noxo groups,

R² is (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl,(C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl, (C₃-C₆) halocycloalkyl,(C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, phenyl,phenyl-(C₁-C₆)-alkyl, heteroaryl, (C₁-C₆)-alkylheteroaryl, heterocyclyl,(C₁-C₆) alkylheterocyclyl, (C₁-C₆)-alkyl-O-heteroaryl,(C₁-C₆)-alkyl-O-heterocyclyl, (C₁-C₆)-alkyl-NR³-heteroaryl,(C₁-C₆)-alkyl-NR³-heterocyclyl, where the 21 latter radicals aresubstituted by s radicals from the group consisting of cyano, halogen,nitro, thiocyanato, OR³, S(O)_(n)R⁴, N(R³)₂, NR³OR³, COR³, OCOR³, SCOR⁴,NR³COR³, NR³SO₂R⁴, CO₂R³, COSR⁴, CON(R³)₂ and(C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and where heterocyclyl bears noxo groups,

R³ is hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,(C₃-C₆)-cycloalkyl or (C₃-C₆)cycloalkyl-(C₁-C₆)-alkyl,

R⁴ is (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl or (C₂-C₆)-alkynyl,(C₃-C₆)-cycloalkyl or (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,

R⁵ is (C₁-C₄)-alkyl,

n is 0, 1 or 2,

s is 0, 1, 2 or 3,

A is an A1, A2, A3 or A4 radical

B represents N or CH,

R is (C₁-C₆)-alkyl-OC(O)N(R³)₂ or (C₁-C₆)-alkyl-OC(O)OR¹²,

R⁶ is (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₂-C₆)-alkynyl,

where these 6 aforementioned radicals are each substituted by s radicalsfrom the group consisting of nitro, cyano, SiR⁹ ₃, PO(OR⁹)₃,S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy, N(R⁷)₂,COR⁷, CO₂R⁷, OCOR⁷, OCO₂R⁷, NR⁷COR⁷, NR⁷SO₂R⁸, (C₃-C₆)-cycloalkyl,heteroaryl, heterocyclyl, phenyl, D-heteroaryl, D-heterocyclyl, D-phenylor D-benzyl, and where the 7 latter radicals are substituted by sradicals from the group of methyl, ethyl, methoxy, trifluoromethyl andhalogen, and where heterocyclyl bears n oxo groups, or

R⁶ is (C₃-C₇)-cycloalkyl, heteroaryl, heterocyclyl or phenyl, eachsubstituted by s radicals from the group consisting of halogen, nitro,cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,S(O)_(n)-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy and(C₁-C₆)-alkoxy-(C₁-C₄)-alkyl,

R⁷ is hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,(C₃-C₆)-cycloalkyl or (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl or phenyl,

R⁸ is (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl or phenyl,

R⁹ is (C₁-C)-alkyl,

R¹⁰ is (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy orhalo-(C₁-C₆)-alkoxy,

R¹¹ is (C₁-C₆)-alkyl or halo-(C₁-C₆)-alkyl,

R¹² is (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl or (C₁-C₆)-cycloalkyl,

s is 0, 1, 2 or 3,

n is 0, 1 or 2,

D is O, S, or NR⁸.

Preference is given to compounds of the general formula (I) in which

R⁶ is (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,(C₂-C₆)-alkynyl, where these 4 aforementioned radicals are eachsubstituted by s radicals from the group consisting ofS(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy, N(R⁷)₂,COR⁷, CO₂R⁷, OCOR⁷, OCO₂R⁷, NR⁷COR⁷, NR⁷SO₂R⁸, (C₃-C₆)-cycloalkyl,heteroaryl, heterocyclyl, phenyl, D-heteroaryl, D-heterocyclyl, D-phenylor D-benzyl, and where the 7 latter radicals are substituted by sradicals from the group of methyl, ethyl, methoxy, trifluoromethyl andhalogen, and where heterocyclyl bears n oxo groups, or R⁶ is(C₃-C₇)-cycloalkyl, heteroaryl, heterocyclyl or phenyl, each substitutedby s radicals from the group consisting of halogen, nitro, cyano,(C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy and(C₁-C₆)-alkoxy-(C₁-C₄)-alkyl,

and the other substituents and indices have the respective definitionsgiven above.

Particular preference is given to compounds of the general formula (I)in which W is CY,

X and Z are each independently hydrogen, halogen, (C₁-C₆)-alkyl, (C₁-C₆)haloalkyl, (C₂-C₆)-alkenyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-halocycloalkyl,OR¹, S(O)_(n)R², SO₂N(R¹)₂, NR¹SO₂R², NR¹COR¹, (C₁-C₆)-alkyl-S(O)_(n)R²,(C₁-C₆)-alkyl-OR¹, or heteroaryl, heterocyclyl or phenyl, eachsubstituted by s radicals from the group of methyl, ethyl, methoxy,nitro, trifluoromethyl and halogen,

Y is hydrogen, (C₂-C₆)-alkenyl, COR¹, CO₂R¹, OCO₂R¹, NR¹CO₂R¹,C(O)N(R¹)₂, NR¹C(O)N(R¹)₂, OC(O)N(R¹)₂, C(O)N(R¹)OR¹, NR¹SO₂R², NR¹COR¹,OR¹, S(O)_(n)R², SO₂N(R¹)₂, (C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹,(C₁-C₆)-alkyl-OCOR¹, (C₁-C₆)alkyl-CO₂R¹, (C₁-C₆)-alkyl-CON(R¹)₂,(C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R²,N(R¹)₂, CH═NOR¹, (C₁-C₆)-alkyl-CH═NOR¹, (C₁-C₆) alkylheteroaryl,(C₁-C₆)-alkylheterocyclyl, heteroaryl or heterocyclyl, where the 4latter radicals are each substituted by s radicals from the groupconsisting of halogen, nitro, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl, S(O)_(n)-(C₁-C₆)-alkyl, (C₁-C₆) alkoxy,halo-(C₁-C₆)-alkoxy, (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl and cyanomethyl, andwhere heterocyclyl bears n oxo groups,

V is hydrogen, Cl, OMe, methyl or ethyl,

R⁶ is methyl, ethyl or n-propyl,

and the other substituents and indices have the respective definitionsgiven above.

Very particularly preference is given to compounds of the generalformula (I) in which

X is F, Cl, Br, methyl, ethyl, cyclopropyl, trifluoromethyl, methoxy,methoxymethyl, methoxyethoxymethyl, SMe or SO₂Me,

Z is hydrogen, F, Cl, Br, I, methyl, ethyl, trifluoromethyl,difluoromethyl, pentafluoroethyl, methylsulfonyl or ethylsulfonyl,

Y is hydrogen, SMe, S(O)Me, SO₂Me, SEt, S(O)Et, SO₂Et, CH₂OMe, CH₂OEt,CH₂OCH₂CF₃, CH₂SMe, CH₂S(O)Me, CH₂SO₂Me, vinyl, C(O)Me, C(O)Et, C(O)cPr,CO₂Me, CHN═OMe, 4,5-dihydro-1,2-oxazol-3-yl,5-methyl-4,5-dihydro-1,2-oxazol-3-yl,5-methyl-4,5-dihydro-1,2-oxazol-3-yl,5-cyanomethyl-4,5-dihydro-1,2-oxazol-3-yl, 4,5-dihydro-1,2-oxazol-5-yl,3-methyl-4,5-dihydro-1,2-oxazol-5-yl, 1H-pyrazol-1-yl,1H-1,2,3-triazol-1-yl, 2H-1,2,3-triazol-2-yl, 1H-1,2,4-triazol-1-yl,pyrolidin-2-on-1-yl, morpholin-3-on-4-yl, OMe, OEt, O-n-Pr, OCH₂-c-Pr,OCH₂CH₂F; OCH₂CH₂OMe or OCH₂CH₂CH₂OMe,

V is hydrogen,

B is N,

R is CH₂OCO₂Et, CH(CH₃)OCO₂Me, CH(CH₃)OCO₂Et, CH(CH₃)OCO₂-c-hexyl,CH(CH₃)OCO₂-i-Pr or CH(CH₃)OCO₂-t-Bu,

R⁶ is methyl or ethyl,

and the other substituents and indices have the respective definitionsgiven above.

In the formula (I) and all the formulae which follow, alkyl radicalshaving more than two carbon atoms may be straight-chain or branched.Alkyl radicals are, for example, methyl, ethyl, n-propyl or isopropyl,n-, iso-, t- or 2-butyl, pentyls, hexyls such as n-hexyl, isohexyl and1,3-dimethylbutyl. Analogously, alkenyl is, for example, allyl,1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl,but-3-en-1-yl, 1-methylbut-3-en-1-yl and 1-methylbut-2-en-1-yl. Alkynylis, for example, propargyl, but-2-yn-1-yl, but-3-yn-1-yl,1-methylbut-3-yn-1-yl. The multiple bond may be in any position in eachunsaturated radical. Cycloalkyl is a carbocyclic saturated ring systemhaving three to six carbon atoms, for example cyclopropyl, cyclobutyl,cyclopentyl or cyclohexyl. Analogously, cycloalkenyl is a monocyclicalkenyl group having three to six carbon ring members, for examplecyclopropenyl, cyclobutenyl, cyclopentenyl and cyclohexenyl, where thedouble bond may be in any position.

Halogen represents fluorine, chlorine, bromine or iodine.

Heterocyclyl is a saturated, partly saturated or fully unsaturatedcyclic radical which contains 3 to 6 ring atoms, of which 1 to 4 arefrom the group of oxygen, nitrogen and sulfur, and which mayadditionally be fused by a benzo ring. For example, heterocyclyl ispiperidinyl, pyrrolidinyl, tetrahydrofuranyl, dihydrofuranyl andoxetanyl.

Heteroaryl is an aromatic cyclic radical which contains 3 to 6 ringatoms, of which 1 to 4 are from the group of oxygen, nitrogen andsulfur, and which may additionally be fused by a benzo ring. Forexample, heteroaryl is benzimidazol-2-yl, furanyl, imidazolyl,isoxazolyl, isothiazolyl, oxazolyl, pyrazinyl, pyrimidinyl, pyridazinyl,pyridinyl, benzisoxazolyl, thiazolyl, pyrrolyl, pyrazolyl, thiophenyl,1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl,1,3,4-oxadiazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, 1,2,5-triazolyl,1,3,4-triazolyl, 1,2,4-triazolyl, 1,2,4-thiadiazolyl,1,3,4-thiadiazolyl, 1,2,3-thiadiazolyl, 1,2,5-thiadiazolyl,2H-1,2,3,4-tetrazolyl, 1H-1,2,3,4-tetrazolyl, 1,2,3,4-oxatriazolyl,1,2,3,5-oxatriazolyl, 1,2,3,4-thiatriazolyl and 1,2,3,5-thiatriazolyl.

If a group is polysubstituted by radicals, this should be understood tomean that this group is substituted by one or more identical ordifferent radicals selected from the radicals mentioned. The sameapplies to the formation of ring systems by different atoms andelements.

Depending on the nature of the substituents and the manner in which theyare attached, the compounds of the general formula (I) may be present asstereoisomers. If, for example, one or more asymmetric carbon atoms arepresent, enantiomers and diastereomers may occur. Stereoisomers likewiseoccur when n is 1 (sulfoxides). Stereoisomers can be obtained from themixtures obtained in the preparation by customary separation methods,for example by chromatographic separation processes. It is likewisepossible to selectively prepare stereoisomers by using stereoselectivereactions with use of optically active starting materials and/orauxiliaries. The invention also relates to all the stereoisomers andmixtures thereof that are encompassed by the general formula (I) but arenot defined specifically. Owing to the oxime ether structure, thecompounds of the invention may also occur as geometric isomers (E/Zisomers). The invention also relates to all E/Z isomers and mixturesthereof which are encompassed by the general formula (I) but not definedspecifically.

The compounds according to the invention may be prepared, for example,by the method shown in scheme 1, by reacting an N-(tetrazol-5-yl)- orN-(triazol-5-yl)arylcarboxamide or -nicotinamide (II) with a compound ofthe general formula (III), where L is a leaving group, for example achlorine, bromine, iodine, mesyloxy, tosyloxy, trifluorosulfonyloxy,etc.:

The compounds of the formula (I) according to the invention are obtainedin principle as a mixture of the compounds of formulae (I-A1), (IA-2),(I-A3) and (I-A4) and may be isolated by simple methods known to thoseskilled in the art such as chromatographic separation orrecrystallization.

The N-(tetrazol-5-yl)- or N-(triazol-5-yl)arylcarboxamides (II) of theformula (II) are known in principle and may be prepared by the methodsdescribed in WO 2012/028579 A1. The compounds of the formula (III) inwhich L is a leaving group such as chlorine, bromine, iodine,methylsulfonyloxy, tosyloxy or trifluorosulfonyloxy are eithercommercially available or can be prepared by known methods described inthe literature.

Collections of compounds of the formula (I) which can be synthesized bythe abovementioned reactions can also be prepared in a parallelizedmanner, in which case this may be accomplished in a manual, partlyautomated or fully automated manner. It is possible, for example, toautomate the conduct of the reaction, the workup or the purification ofthe products and/or intermediates. Overall, this is understood to mean aprocedure as described, for example, by D. Tiebes in CombinatorialChemistry—Synthesis, Analysis, Screening (editor: Günther Jung), Wiley,1999, on pages 1 to 34.

For the parallelized conduct of the reaction and workup, it is possibleto use a number of commercially available instruments, for exampleCalypso reaction blocks from Barnstead International, Dubuque, Iowa52004-0797, USA or reaction stations from Radleys, Shirehill, SaffronWalden, Essex, CB11 3AZ, England, or MuItiPROBE Automated Workstationsfrom Perkin Elmer, Waltham, Mass. 02451, USA. For the parallelizedpurification of compounds of the general formula (I) or of intermediateswhich occur in the course of preparation, available apparatuses includechromatography apparatuses, for example from ISCO, Inc., 4700 SuperiorStreet, Lincoln, Nebr. 68504, USA.

The apparatuses detailed lead to a modular procedure in which theindividual working steps are automated, but manual operations have to becarried out between the working steps. This can be circumvented by usingpartly or fully integrated automation systems in which the respectiveautomation modules are operated, for example, by robots. Automationsystems of this type can be obtained, for example, from Caliper,Hopkinton, Mass. 01748, USA.

The implementation of single or multiple synthesis steps can besupported by the use of polymer-supported reagents/scavenger resins. Thespecialist literature describes a series of experimental protocols, forexample in ChemFiles, Vol. 4, No. 1, Polymer-Supported Scavengers andReagents for Solution-Phase Synthesis (Sigma-Aldrich).

Besides the methods described herein, the preparation of compounds ofthe general formula (I) can take place completely or partially bysolid-phase-supported methods. For this purpose, individualintermediates or all intermediates in the synthesis or a synthesisadapted for the corresponding procedure are bound to a synthesis resin.Solid-phase-supported synthesis methods are described adequately in thetechnical literature, for example Barry A. Bunin in “The CombinatorialIndex”, Academic Press, 1998 and Combinatorial Chemistry—Synthesis,Analysis, Screening (editor: Günther Jung), Wiley, 1999. The use ofsolid-phase-supported synthesis methods permits a number of protocols,which are known from the literature and which for their part may beperformed manually or in an automated manner. The reactions can beperformed, for example, by means of IRORI technology in microreactorsfrom Nexus Biosystems, 12140 Community Road, Poway, Calif. 92064, USA.

Both in the solid and in the liquid phase, the implementation ofindividual or several synthesis steps may be supported by the use ofmicrowave technology. The specialist literature describes a series ofexperimental protocols, for example in Microwaves in Organic andMedicinal Chemistry (editor: C. O. Kappe and A. Stadler), Wiley, 2005.

The preparation by the processes described herein gives compounds of theformula (I) in the form of substance collections, which are calledlibraries. The present invention also provides libraries comprising atleast two compounds of the formula (I).

The compounds according to the invention of the formula (I), referred tohereinbelow as “compounds according to the invention”, have an excellentherbicidal effectiveness against a broad spectrum of economicallyimportant mono- and dicotyledonous annual weeds. The active ingredientsalso have good control over perennial harmful plants which are difficultto control and produce shoots from rhizomes, root stocks or otherperennial organs.

The present invention therefore also provides a method for controllingunwanted plants or for regulating the growth of plants, preferably inplant crops, in which one or more compound(s) of the invention is/areapplied to the plants (for example harmful plants such asmonocotyledonous or dicotyledonous weeds or unwanted crop plants), theseed (for example grains, seeds or vegetative propagules such as tubersor shoot parts with buds) or the area on which the plants grow (forexample the area under cultivation). The compounds of the invention canbe deployed, for example, prior to sowing (if appropriate also byincorporation into the soil), prior to emergence or after emergence.Specific examples of some representatives of the monocotyledonous anddicotyledonous weed flora which can be controlled by the compounds ofthe invention are as follows, though the enumeration is not intended toimpose a restriction to particular species.

Monocotyledonous harmful plants of the genera: Aegilops, Agropyron,Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus,Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa,Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis,Heteranthera, Imperata, lschaemum, Leptochloa, Lolium, Monochoria,Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria,Scirpus, Setaria, Sorghum.

Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia,Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella,Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura,Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium,Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria,Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago,Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex,Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea,Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola,Xanthium.

If the compounds of the invention are applied to the soil surface beforegermination, either the emergence of the weed seedlings is preventedcompletely or the weeds grow until they have reached the cotyledonstage, but then they stop growing and ultimately die completely afterthree to four weeks have passed.

If the active compounds are applied post-emergence to the green parts ofthe plants, growth stops after the treatment, and the harmful plantsremain at the growth stage of the point of time of application, or theydie completely after a certain time, so that in this manner competitionby the weeds, which is harmful to the crop plants, is eliminated veryearly and in a sustained manner.

Although the compounds of the invention have outstanding herbicidalactivity against monocotyledonous and dicotyledonous weeds, crop plantsof economically important crops, for example dicotyledonous crops of thegenera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus,Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana,Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous crops of thegenera Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum,Saccharum, Secale, Sorghum, Triticale, Triticum, Zea, in particular Zeaand Triticum, will be damaged to a negligible extent only, if at all,depending on the structure of the particular compound of the inventionand its application rate. For these reasons, the present compounds arevery suitable for selective control of unwanted plant growth in plantcrops such as agriculturally useful plants or ornamental plants.

In addition, the compounds of the invention (depending on theirparticular structure and the application rate deployed) have outstandinggrowth-regulating properties in crop plants. They intervene in theplants' own metabolism with regulatory effect, and can thus be used forthe controlled influencing of plant constituents and to facilitateharvesting, for example by triggering desiccation and stunted growth.Furthermore, they are also suitable for the general control andinhibition of unwanted vegetative growth without killing the plants inthe process. Inhibition of vegetative growth plays a major role for manymono- and dicotyledonous crops since, for example, this can reduce orcompletely prevent lodging.

By virtue of their herbicidal and plant growth regulatory properties,the active compounds can also be used to control harmful plants in cropsof genetically modified plants or plants modified by conventionalmutagenesis. In general, the transgenic plants are characterized byparticular advantageous properties, for example by resistances tocertain pesticides, in particular certain herbicides, resistances toplant diseases or pathogens of plant diseases, such as certain insectsor microorganisms such as fungi, bacteria or viruses. Other particularproperties relate, for example, to the harvested material with regard toquantity, quality, storability, composition and specific constituents.For instance, there are known transgenic plants with an elevated starchcontent or altered starch quality, or those with a different fatty acidcomposition in the harvested material.

It is preferable, with respect to transgenic crops, to use the compoundsof the invention in economically important transgenic crops of usefulplants and ornamentals, for example of cereals such as wheat, barley,rye, oats, millet/sorghum, rice and corn or else crops of sugar beet,cotton, soybean, oilseed rape, potato, tomato, peas and other types ofvegetable. It is preferred to employ the compounds of the invention asherbicides in crops of useful plants which are resistant, or have beenmade resistant by genetic engineering, to the phytotoxic effects of theherbicides.

It is preferred to use the compounds of the invention in economicallyimportant transgenic crops of useful plants and ornamentals, for exampleof cereals such as wheat, barley, rye, oats, millet/sorghum, rice,cassava and corn or else crops of sugar beet, cotton, soybean, oilseedrape, potato, tomato, peas and other vegetables. Preferably, thecompounds of the invention can be used as herbicides in crops of usefulplants which are resistant, or have been made resistant by geneticengineering, to the phytotoxic effects of the herbicides.

Conventional ways of producing novel plants which have modifiedproperties in comparison to existing plants consist, for example, intraditional cultivation methods and the generation of mutants.Alternatively, novel plants with modified properties can be generatedwith the aid of recombinant methods (see, for example, EP-A-0221044,EP-A-0131624). For example, there have been descriptions in severalcases of:

-   -   genetic modifications of crop plants for the purpose of        modifying the starch synthesized in the plants (e.g. WO        92/11376, WO 92/14827, WO 91/19806),    -   transgenic crop plants which are resistant to particular        herbicides of the glufosinate type (cf., for example,        EP-A-0242236, EP-A-242246) or glyphosate type (WO 92/00377) or        the sulfonylurea type (EP-A-0257993, U.S. Pat. No. 5,013,659),    -   transgenic crop plants, for example cotton, capable of producing        Bacillus thuringiensis toxins (Bt toxins), which make the plants        resistant to particular pests (EP-A-0142924, EP-A-0193259).    -   transgenic crop plants with a modified fatty acid composition        (WO 91/13972),    -   genetically modified crop plants with novel constituents or        secondary metabolites, for example novel phytoalexins, which        bring about an increased disease resistance (EPA 309862,        EPA0464461),    -   genetically modified plants having reduced photorespiration,        which have higher yields and higher stress tolerance (EPA        0305398),    -   transgenic crop plants which produce pharmaceutically or        diagnostically important proteins (“molecular pharming”),    -   transgenic crop plants which feature higher yields or better        quality,    -   transgenic crop plants which feature, for example, the        abovementioned novel properties (“gene stacking”) through        combinations.

Numerous molecular biology techniques which can be used to produce noveltransgenic plants with modified properties are known in principle; see,for example, I. Potrykus and G. Spangenberg (eds.) Gene Transfer toPlants, Springer Lab Manual (1995), Springer Verlag Berlin, Heidelberg,or Christou, “Trends in Plant Science” 1 (1996) 423-431).

For such recombinant manipulations, nucleic acid molecules which allowmutagenesis or sequence alteration by recombination of DNA sequences canbe introduced into plasmids. With the aid of standard methods, it ispossible, for example, to undertake base exchanges, remove parts ofsequences or add natural or synthetic sequences. To join the DNAfragments with one another, adapters or linkers can be placed onto thefragments, see, for example, Sambrook et al., 1989, Molecular Cloning, ALaboratory Manual, 2nd edition Cold Spring Harbor Laboratory Press, ColdSpring Harbor, N.Y., or Winnacker “Gene and Klone [Genes and clones]”,VCH Weinheim 2nd edition 1996.

For example, the generation of plant cells with a reduced activity of agene product can be achieved by expressing at least one correspondingantisense RNA, a sense RNA for achieving a cosuppression effect, or byexpressing at least one suitably constructed ribozyme which specificallycleaves transcripts of the abovementioned gene product. To this end, itis firstly possible to use DNA molecules which encompass the entirecoding sequence of a gene product inclusive of any flanking sequenceswhich may be present, and also DNA molecules which only encompassportions of the coding sequence, in which case it is necessary for theseportions to be long enough to have an antisense effect in the cells. Itis also possible to use DNA sequences which have a high degree ofhomology to the coding sequences of a gene product, but are notcompletely identical to them.

When expressing nucleic acid molecules in plants, the proteinsynthesized may be localized in any desired compartment of the plantcell. However, to achieve localization in a particular compartment, itis possible, for example, to join the coding region to DNA sequenceswhich ensure localization in a particular compartment. Such sequencesare known to those skilled in the art (see, for example, Braun et al.,EMBO J. 11 (1992), 3219-3227, Wolter et al., Proc. Natl. Acad. Sci. USA85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106). Thenucleic acid molecules can also be expressed in the organelles of theplant cells.

The transgenic plant cells can be regenerated by known techniques togive rise to entire plants. In principle, the transgenic plants may beplants of any desired plant species, i.e. not only monocotyledonous butalso dicotyledonous plants.

Thus, transgenic plants can be obtained whose properties are altered byoverexpression, suppression or inhibition of homologous (=natural) genesor gene sequences or expression of heterologous (=foreign) genes or genesequences.

The compounds of the invention can be used with preference in transgeniccrops which are resistant to growth regulators, for example dicamba, orto herbicides which inhibit essential plant enzymes, for exampleacetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS)or hydroxyphenylpyruvate dioxygenases (HPPD), or to herbicides from thegroup of the sulfonylureas, the glyphosates, glufosinates orbenzoylisoxazoles and analogous active ingredients.

When the active compounds of the invention are employed in transgeniccrops, not only do the effects toward harmful plants observed in othercrops occur, but frequently also effects which are specific toapplication in the particular transgenic crop, for example an altered orspecifically widened spectrum of weeds which can be controlled, alteredapplication rates which can be used for the application, preferably goodcombinability with the herbicides to which the transgenic crop isresistant, and influencing of growth and yield of the transgenic cropplants.

The invention therefore also provides for the use of the compounds ofthe invention as herbicides for control of harmful plants in transgeniccrop plants.

A further advantage of the compounds according to the invention alsoconsists of a lower toxicity towards organisms such as insects,amphibians, fish and mammals.

The compounds of the invention can be applied in the form of wettablepowders, emulsifiable concentrates, sprayable solutions, dustingproducts or granules in the customary formulations. The inventiontherefore also provides herbicidal and plant-growth-regulatingcompositions which comprise the compounds of the invention.

The compounds of the invention can be formulated in various ways,according to the biological and/or physicochemical parameters required.Possible formulations include, for example: wettable powders (WP),water-soluble powders (SP), water-soluble concentrates, emulsifiableconcentrates (EC), emulsions (EW), such as oil-in-water and water-in-oilemulsions, sprayable solutions, suspension concentrates (SC),dispersions based on oil or water, oil-miscible solutions, capsulesuspensions (CS), dusting products (DP), dressings, granules forscattering and soil application, granules (GR) in the form ofmicrogranules, spray granules, absorption and adsorption granules,water-dispersible granules (WG), water-soluble granules (SG), ULVformulations, microcapsules and waxes.

These individual formulation types are known in principle and aredescribed, for example, in: Winnacker-Kuchler, “Chemische Technologie”[Chemical Technology], volume 7, C. Hanser Verlag Munich, 4th Ed. 1986,Wade van Valkenburg, “Pesticide Formulations”, Marcel Dekker, N.Y.,1973, K. Martens, “Spray Drying” Handbook, 3rd Ed. 1979, G. Goodwin Ltd.London.

The formulation auxiliaries required, such as inert materials,surfactants, solvents and further additives, are likewise known and aredescribed, for example, in: Watkins, “Handbook of Insecticide DustDiluents and Carriers”, 2nd Ed., Darland Books, Caldwell N.J.; H.v.Olphen, “Introduction to Clay Colloid Chemistry”, 2nd Ed., J. Wiley &Sons, N.Y.; C. Marsden, “Solvents Guide”, 2nd Ed., Interscience, N.Y.1963; McCutcheon's “Detergents and Emulsifiers Annual”, MC Publ. Corp.,Ridgewood N.J.; Sisley and Wood, “Encyclopedia of Surface ActiveAgents”, Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt,“Grenzflächenaktive Äthylenoxidaddukte” [Interface-active Ethylene OxideAdducts], Wiss. Verlagsgesellschaft, Stuttgart 1976; Winnacker-Küchler,“Chemische Technologie” [Chemical Engineering], volume 7, C. HanserVerlag Munich, 4th Ed. 1986.

On the basis of these formulations, it is also possible to producecombinations with other pesticidally active substances, for exampleinsecticides, acaricides, herbicides, fungicides, and also withsafeners, fertilizers and/or growth regulators, for example in the formof a finished formulation or as a tankmix. Suitable safeners are, forexample, mefenpyr-diethyl, cyprosulfamide, isoxadifen-ethyl,cloquintocet-mexyl and dichlormid.

Wettable powders are preparations which can be dispersed uniformly inwater and, in addition to the active compound, apart from a diluent orinert substance, also comprise surfactants of the ionic and/or nonionictype (wetting agents, dispersants), for example polyoxyethylatedalkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fattyamines, fatty alcohol polyglycol ether sulfates, alkanesulfonates,alkylbenzenesulfonates, sodium lignosulfonate, sodium2,2′-dinaphthylmethane-6,6′-disulfonate, sodiumdibutylnaphthalenesulfonate or else sodium oleoylmethyltaurate. Toproduce the wettable powders, the active herbicidal ingredients arefinely ground, for example in customary apparatuses such as hammermills, blower mills and air-jet mills, and simultaneously orsubsequently mixed with the formulation auxiliaries.

Emulsifiable concentrates are produced by dissolving the active compoundin an organic solvent, for example butanol, cyclohexanone,dimethylformamide, xylene, or else relatively high-boiling aromatics orhydrocarbons or mixtures of the organic solvents, with addition of oneor more ionic and/or nonionic surfactants (emulsifiers). Examples ofemulsifiers which may be used are: calcium alkylarylsulfonates such ascalcium dodecylbenzenesulfonate, or nonionic emulsifiers such as fattyacid polyglycol esters, alkylaryl polyglycol ethers, fatty alcoholpolyglycol ethers, propylene oxide-ethylene oxide condensation products,alkyl polyethers, sorbitan esters, for example sorbitan fatty acidesters, or polyoxyethylene sorbitan esters, for example polyoxyethylenesorbitan fatty acid esters.

Dusting products are obtained by grinding the active compound withfinely distributed solids, for example talc, natural clays, such askaolin, bentonite and pyrophillite, or diatomaceous earth.

Suspension concentrates may be water- or oil-based. They may beprepared, for example, by wet-grinding by means of commercial bead millsand optional addition of surfactants as have, for example, already beenlisted above for the other formulation types.

Emulsions, for example oil-in-water emulsions (EW), can be produced, forexample, by means of stirrers, colloid mills and/or static mixers usingaqueous organic solvents and optionally surfactants as already listedabove, for example, for the other formulation types.

Granules can be produced either by spraying the active compound ontoadsorptive granular inert material or by applying active compoundconcentrates to the surface of carriers, such as sand, kaolinites orgranular inert material, by means of adhesives, for example polyvinylalcohol, sodium polyacrylate or else mineral oils. Suitable activecompounds can also be granulated in the manner customary for theproduction of fertilizer granules - if desired as a mixture withfertilizers.

Water-dispersible granules are produced generally by the customaryprocesses such as spray-drying, fluidized-bed granulation, pangranulation, mixing with high-speed mixers and extrusion without solidinert material.

For the production of pan, fluidized-bed, extruder and spray granules,see e.g. processes in “Spray-Drying Handbook” 3rd Ed. 1979, G. GoodwinLtd., London, J. E. Browning, “Agglomeration”, Chemical and Engineering1967, pages 147 ff.; “Perry's Chemical Engineer's Handbook”, 5th Ed.,McGraw-Hill, New York 1973, pp. 8-57.

For further details regarding the formulation of crop protectioncompositions, see, for example, G. C. Klingman, “Weed Control as aScience”, John Wiley and Sons, Inc., New York, 1961, pages 81-96 and J.D. Freyer, S. A. Evans, “Weed Control Handbook”, 5th Ed., BlackwellScientific Publications, Oxford, 1968, pages 101-103.

The agrochemical preparations contain generally 0.1 to 99% by weight,especially 0.1 to 95% by weight, of compounds of the invention.

In wettable powders, the active compound concentration is, for example,about 10% to 90% by weight, the remainder to 100% by weight consistingof customary formulation constituents. In emulsifiable concentrates, theactive compound concentration may be about 1% to 90% and preferably 5%to 80% by weight. Dust-type formulations contain 1% to 30% by weight ofactive ingredient, preferably usually 5% to 20% by weight of activeingredient; sprayable solutions contain about 0.05% to 80% by weight,preferably 2% to 50% by weight of active ingredient. In the case ofwater-dispersible granules, the active compound content dependspartially on whether the active compound is in liquid or solid form andon which granulation auxiliaries, fillers, etc., are used. In thewater-dispersible granules, the content of active compound is, forexample, between 1% and 95% by weight, preferably between 10% and 80% byweight.

In addition, the active compound formulations mentioned optionallycomprise the respective customary stickers, wetters, dispersants,emulsifiers, penetrants, preservatives, antifreeze agents and solvents,fillers, carriers and dyes, defoamers, evaporation inhibitors and agentswhich influence the pH and the viscosity.

For application, the formulations in commercial form are, ifappropriate, diluted in a customary manner, for example in the case ofwettable powders, emulsifiable concentrates, dispersions andwater-dispersible granules with water. Dust-type preparations, granulesfor soil application or granules for scattering and sprayable solutionsare not normally diluted further with other inert substances prior toapplication.

The required application rate of the compounds of the formula (I) varieswith the external conditions, including, inter alia, temperature,humidity and the type of herbicide used. It can vary within wide limits,for example between 0.001 and 1.0 kg/ha or more of active substance, butit is preferably between 0.005 and 750 g/ha.

The examples which follow illustrate the invention.

A. CHEMICAL EXAMPLES

1. Synthesis of1-(5-{[2-chloro-3-(methylsulfanyl)-4-(trifluoromethyl)benzoyl]imino}-4-methyl-4,5-dihydro-1H-tetrazol-1-yl)ethylethyl carbonate (Table example No. 1-384) and1-[(ethoxycarbonyl)oxy]ethyl2-chloro-3-(methylsulfanyl)-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzenecarboximidate(Table example No. 19-384):

To a solution of 1.00 g (2.843 mmol) of2-chloro-3-(methylsulfanyI)-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamideare in 20 ml of acetonitrile are added at room temperature 911 mg (5.97mmol) of 1-chloroethyl ethyl carbonate and 825 mg (5.97 mmol) ofpotassium carbonate and the mixture is boiled under reflux for 9 h. Thereaction mixture is concentrated and then dissolved in 20 ml of ethylacetate and 20 ml of water are added and extracted. The aqueous phase isextracted twice more with 20 ml of ethyl acetate each time. The combinedorganic phases are washed with saturated NaCI solution, dried andconcentrated. The residue is purified by RP-HPLC (acetonitrile/water).

Compound no. 1-384

Yield: 230 mg (15.7%)

¹H-NMR (400 MHz; CDCl₃): 7.78 ppm (d, 1H), 7.67 ppm (d, 1H), 7.03 (q,1H), 4.25-4.16 (m, 2H); 3.97 (s, 3H); 2.43 (s, 3H); 2.00 (d, 3H), 1.29(t; 3H).

Compound no. 19-384

Yield: 200 mg (13.5%)

¹H-NMR (400 MHz; CDCl₃): 8.04 ppm (d, 1H), 7.81 ppm (d, 1H), 6.74 (q,1H), 4.25-4.18 (m, 2H); 3.25 (s, 3H); 2.92 (s, 3H); 2.49 (s, 3H); 1.77(d, 3H), 1.30 (t; 3H).

2. Synthesis of1-(5-{[2-chloro-3-(methylsulfanyl)-4-(trifluoromethyl)benzoyl]imino}-4-methyl-4,5-dihydro-1H-tetrazol-1-yl)ethylmethyl carbonate (Table example No. 3-384) and

1-[(Methoxycarbonyl)oxy]ethyl2-chloro-3-(methylsulfanyl)-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzenecarboximidate(Table example No. 21-384)

By analogy to the abovementioned preparation method, by reacting 1.00 g(2.843 mmol) of2-chloro-3-(methylsulfanyl)-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamidewith 871 mg (5.71 mmol) of 1-chloroethyl ethyl carbonate, isolated were:

Compound no. 3-384

¹H-NMR (400 MHz; CDCl₃): 7.78 ppm (d, 1H), 7.68 ppm (d, 1H), 7.04 (q,1H), 3.98 (s, 3H); 3.80 (s, 3H), 2.43 (s, 3H); 2.00 (d, 3H).

Compound no. 21-384

¹H-NMR (400 MHz; CDCl₃): 7.73 ppm (d, 1H), 7.53 ppm (d, 1H), 7.28 (q,1H), 3.97 (s, 3H); 3.86 (s, 3H); 2.33 (s, 3H), 1.75 (d, 3H).

3. Synthesis of1-(5-{[2-chloro-3-(methylsulfanyl)-4-(trifluoromethyl)benzoyl]imino}-4-methyl-4,5-dihydro-1H-tetrazol-1-yl)ethylcyclohexyl carbonate (Table example No. 5-384) and1-{[(cyclohexyloxy)carbonyl]oxy}ethyl2-chloro-3-(methylsulfanyl)-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzenecarboximidate(Table example No. 23-384):

By analogy to the abovementioned preparation method, by reacting 1.00 g(2.719 mmol) of2-chloro-3-(methylsulfanyl)-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamidewith 1234 mg (5.97 mmol) of 1-chloroethyl cyclohexyl carbonate, isolatedwere:

Compound no. 5-384

¹H-NMR (400 MHz; CDCl₃): 7.77 ppm (d, 1H), 7.68 ppm (d, 1H), 7.00 (q,1H), 4.65-4.59 (m, 1H), 3.98 (s, 3H); 2.43 (s, 3H); 2.00 (d, 3H);1.98-1.88 (m, 1H), 1.85-1.65 (m, 4H),1.59-1.18 (m, 5H).

Compound no. 23-384

¹H-NMR (400 MHz; CDCl₃): 7.96 ppm (d, 1H), 7.73 ppm (d, 1H), 7.54 ppm(d, 1H), 7.27 (q, 1H), 4.72-4.63 (m, 1H), 3.97 (s, 3H); 2.32 (s, 3H);2.00- 1.86 (m, 2H), 1.77-1.65 (m, 5H), 1.59-1.21 (m, 6H).

Compound no. 32-384

¹H-NMR (400 MHz; CDCl₃): 7.81 ppm and 7.72 ppm (2d, 1H), 7.52 ppm and7.38 (2d, 1H), 6.23 and 5.95 (2q, 1H), 4.72 and 4.56 (2m, 1H), 4.12-3.98(3s, 3H); 2.2.46 and 2.34 (2s, 3H); 2.01- 1.766 (m, 4H), 1.59-1.1.22 (m,8H).

4. Synthesis of1-(5-{[2-chloro-4-methyl-3-(methylsulfonyl)benzoyl]imino}-4-methyl-4,5-dihydro-1H-tetrazol-1-yl)ethylethyl carbonate (Table example No. 1-390), 1-[(ethoxycarbonyl)oxy]ethyl2-chloro-4-methyl-3-(methylsulfonyl)-N-(1-methyl-1H-tetrazol-5-yl)benzenecarboximidate(Table exanple No. 19-390) and1-{[2-chloro-4-methyl-3-(methylsulfonyl)benzoyl](1-methyl-1H-tetrazol-5-yl)amino}ethylethyl carbonate (Table example No. 28-390):

To a solution of 100 mg (0.303 mmol) of2-chloro-4-methyl-3-(methylsulfonyl)-N-(1-methyl-1H-tetrazol-5-yl)benzamide in 3 ml of acetonitrile are added at room temperature 49 mg(0.318 mmol) of 1-chloroethyl ethyl carbonate and 104 mg (5.97 mmol) ofcesium carbonate. The mixture is heated to 75° C. for 5 d and stirred atRT until reaction is complete (LC-MS monitoring). The reaction mixtureis filtered and the solvent is removed under reduced pressure. Theresidue is purified by RP-HPLC (acetonitrile/water).

Compound no. 1-390

Yield: 32 mg (24%)

¹H-NMR (400 MHz; CDCl₃): 7.80 ppm (d, 1H), 7.27 ppm (d, 1H), 7.01 (q,1H), 4.23-4.19 (m, 2H); 3.95 (s, 3H); 3.34 (s, 3H); 2.78 (s, 3H), 2.00(d, 3H), 1.29 (t; 3H).

Compound no. 19-390

Yield: 26 mg (19%)

¹H-NMR (400 MHz; CDCl₃): 7.96 ppm (d, 1H), 7.50 ppm (d, 1H), 7.34 ppm(d, 1H), 7.26 (q, 1H), 4.27-4.24 (m, 2H); 3.96 (s, 3H); 3.20 (s, 3H),2.79 (s, 3H); 1.74 (d, 3H), 1.34 (t; 3H).

Compound no. 28-390

Yield: 36 mg (27%)

¹H-NMR (400 MHz; CDCl₃): 7.96 ppm (d, 1H), 7.72 ppm (br, 1H), 7.49 ppm(d, 1H), 6,48 (br, 1H), 4.17 (q, 2H); 4.01 (s, 3H); 3.31 (s, 3H), 2.69(s, 3H); 1.39 (d, 3H), 1.23 (t; 3H).

The examples listed in the tables below were prepared analogously to theabovementioned methods or are obtainable analogously to theabovementioned methods. The compounds listed in the tables below arevery particularly preferred.

TABLE 1 Compounds of the general formula (I) according to the invention,where A is A1, B is N, R⁶ is methyl, R is CH(Me)OCO₂Et, W is CY and V ishydrogen

Physical data No. X Y Z (¹H NMR, DMSO-d₆, 400 MHz) 1-1  F H Cl 1-2  F HSO₂Me 1-3  F H SO₂Et 1-4  F H CF₃ 1-5  F H NO₂ 1-6  Cl H Br 1-7  Cl HSMe 1-8  Cl H SOMe 1-9  Cl H SO₂Me 1-10  Cl H SO₂CH₂Cl 1-11  Cl H SEt1-12  Cl H SO₂Et 1-13  Cl H CF₃ 1-14  Cl H NO₂ 1-15  Cl H pyrazol-1-yl1-16  Cl H 1H-1,2,4- triazol-1-yl 1-17  Br H Cl 1-18  Br H Br 1-19  Br HSO₂Me 1-20  Br H SO₂Et 1-21  Br H CF₃ 1-22  SO₂Me H Cl 1-23  SO₂Me H Br1-24  SO₂Me H SMe 1-25  SO₂Me H SOMe 1-26  SO₂Me H SO₂Me 1-27  SO₂Me HSO₂Et 1-28  SO₂Me H CF₃ 1-29  SO₂Et H Cl 1-30  SO₂Et H Br 1-31  SO₂Et HSMe 1-32  SO₂Et H SOMe 1-33  SO₂Et H SO₂Me 1-34  SO₂Et H CF₃ 1-35  NO₂ HF 1-36  NO₂ H Cl 1-37  NO₂ H Br 1-38  NO₂ H I 1-39  NO₂ H CN 1-40  NO₂ HSO₂Me 1-41  NO₂ H SO₂Et 1-42  NO₂ H CF₃ 1-43  Me H Cl 1-44  Me H Br1-45  Me H SMe 1-46  Me H SO₂Me 1-47  Me H SO₂CH₂Cl 1-48  Me H SEt 1-49 Me H SO₂Et 1-50  Me H CF₃ 1-51  CH₂SO₂Me H CF₃ 1-52  Et H Cl 1-53  Et HBr 1-54  Et H SMe 1-55  Et H SO₂Me 1-56  Et H SO₂CH₂Cl 1-57  Et H SEt1-58  Et H SO₂Et 1-59  Et H CF₃ 1-60  CF₃ H Cl 1-61  CF₃ H Br 1-62  CF₃H SO₂Me 1-63  CF₃ H SO₂Et 1-64  CF₃ H CF₃ 1-65  NO₂ NH₂ F 1-66  NO₂ NHMeF 1-67  NO₂ NMe₂ F 1-68  NO₂ Me Cl 1-69  NO₂ NH₂ Cl 1-70  NO₂ NHMe Cl1-71  NO₂ NMe₂ Cl 1-72  NO₂ NH₂ Br 1-73  NO₂ NHMe Br 1-74  NO₂ NMe₂ Br1-75  NO₂ NH₂ CF₃ 1-76  NO₂ NMe₂ CF₃ 1-77  NO₂ NH₂ SO₂Me 1-78  NO₂ NH₂SO₂Et 1-79  NO₂ NHMe SO₂Me 1-80  NO₂ NMe₂ SO₂Me 1-81  NO₂ NMe₂ SO₂Et1-82  NO₂ NH₂ 1H-1,2,4- triazol-1-yl 1-83  NO₂ NHMe 1H-1,2,4-triazol-1-yl 1-84  NO₂ NMe₂ 1H-1,2,4- triazol-1-yl 1-85  Me SMe H 1-86 Me SOMe H 1-87  Me SO₂Me H 1-88  Me SEt H 1-89  Me SOEt H 1-90  Me SO₂EtH 1-91  Me S(CH₂)₂OMe H 1-92  Me SO(CH₂)₂OMe H 1-93  Me SO₂(CH₂)₂OMe H1-94  Me F F 1-95  Me F Cl 1-96  Me SEt F 1-97  Me SOEt F 1-98  Me SO₂EtF 1-99  Me Me Cl 1-100 Me F Cl 1-101 Me Cl Cl 1-102 Me NH₂ Cl 1-103 MeNHMe Cl 1-104 Me NMe₂ Cl 1-105 Me O(CH₂)₂OMe Cl 1-106 Me O(CH₂)₃OMe Cl1-107 Me O(CH₂)₄OMe Cl 1-108 Me OCH₂CONMe₂ Cl 1-109 Me O(CH₂)₂—CO—NMe₂Cl 1-110 Me O(CH₂)₂—NH(CO)NMe₂ Cl 1-111 Me O(CH₂)₂—NH(CO)NHCO₂Et Cl1-112 Me O(CH₂)₂—NHCO₂Me Cl 1-113 Me OCH₂—NHSO₂cPr Cl 1-114 MeO(CH₂)-5-2,4-dimethyl- Cl 2,4-dihydro-3H- 1,2,4-triazol-3-one 1-115 MeO(CH₂)-3,5-dimethyl- Cl 1,2-oxazol-4-yl 1-116 Me SMe Cl 1-117 Me SOMe Cl1-118 Me SO₂Me Cl 1-119 Me SEt Cl 1-120 Me SOEt Cl 1-121 Me SO₂Et Cl1-122 Me S(CH₂)₂OMe Cl 1-123 Me SO(CH₂)₂OMe Cl 1-124 Me SO₂(CH₂)₂OMe Cl1-125 Me NH₂ Br 1-126 Me NHMe Br 1-127 Me NMe₂ Br 1-128 Me OCH₂(CO)NMe₂Br 1-129 Me O(CH₂)-5-pyrrolidin-2-one Br 1-130 Me SMe Br 1-131 Me SOMeBr 1-132 Me SO₂Me Br 1-133 Me SEt Br 1-134 Me SOEt Br 1-135 Me SO₂Et Br1-136 Me SMe I 1-137 Me SOMe I 1-138 Me SO₂Me I 1-139 Me SEt I 1-140 MeSOEt I 1-141 Me SO₂Et I 1-142 Me Cl CF₃ 1-143 Me SMe CF₃ 1-144 Me SOMeCF₃ 1-145 Me SO₂Me CF₃ 1-146 Me SEt CF₃ 1-147 Me SOEt CF₃ 1-148 Me SO₂EtCF₃ 1-149 Me S(CH₂)₂OMe CF₃ 1-150 Me SO(CH₂)₂OMe CF₃ 1-151 MeSO₂(CH₂)₂OMe CF₃ 1-152 Me Me SO₂Me 1-153 Me 4,5-dihydro-1,2- SO₂Meoxazol-3-yl 1-154 Me 4,5-dihydro-1,2- SO₂Et oxazol-3-yl 1-155 Me5-cyanomethyl-4,5- SO₂Me dihydro-1,2-oxazol-3-yl 1-156 Me5-cyanomethyl-4,5- SO₂Et dihydro-1,2-oxazol-3-yl 1-157 Me NH₂ SO₂Me1-158 Me NHMe SO₂Me 1-159 Me NMe₂ SO₂Me 1-160 Me NH(CH₂)₂OMe SO₂Me 1-161Me pyrazol-1-yl SO₂Me 1-162 Me OH SO₂Me 1-163 Me OMe SO₂Me 1-164 Me OMeSO₂Et 1-165 Me OEt SO₂Me 1-166 Me OEt SO₂Et 1-167 Me O—i-Pr SO₂Me 1-168Me O—i-Pr SO₂Et 1-169 Me O(CH₂)₂OMe SO₂Me 1-170 Me O(CH₂)₂OMe SO₂Et1-171 Me O(CH₂)₃OMe SO₂Me 1-172 Me O(CH₂)₃OMe SO₂Et 1-173 Me O(CH₂)₄OMeSO₂Me 1-174 Me O(CH₂)₄OMe SO₂Et 1-175 Me O(CH₂)₂NHSO2Me SO₂Me 1-176 MeO(CH₂)₂NHSO2Me SO₂Et 1-177 Me OCH₂(CO)NMe₂ SO₂Me 1-178 Me OCH₂(CO)NMe₂SO₂Et 1-179 Me [1,4]dioxan-2- SO₂Me ylmethoxy 1-180 Me [1,4]dioxan-2-SO₂Et ylmethoxy 1-181 Me O(CH₂)₂—O-(3,5- SO₂Me dimethoxypyrimidin-2-yl)1-182 Me Cl SO₂Me 1-183 Me SMe SO₂Me 1-184 Me SOMe SO₂Me 1-185 Me SO₂MeSO₂Me 1-186 Me SO₂Me SO₂Et 1-187 Me SEt SO₂Me 1-188 Me SOEt SO₂Me 1-189Me SO₂Et SO₂Me 1-190 Me S(CH₂)₂OMe SO₂Me 1-191 Me SO(CH₂)₂OMe SO₂Me1-192 Me SO₂(CH₂)₂OMe SO₂Me 1-193 CH₂SMe OMe SO₂Me 1-194 CH₂OMe OMeSO₂Me 1-195 CH₂O(CH₂)₂ NH(CH₂)₂OEt SO₂Me OMe 1-196 CH₂O(CH₂)₂NH(CH₂)₃OEt SO₂Me OMe 1-197 CH₂O(CH₂)₃ OMe SO₂Me OMe 1-198 CH₂O(CH₂)₂NH(CH₂)₂OMe SO₂Me OMe 1-199 CH₂O(CH₂)₂ NH(CH₂)₃OMe SO₂Me OMe 1-200 EtSMe Cl 1-201 Et SO₂Me Cl 1-202 Et SMe CF₃ 1-203 Et SO₂Me CF₃ 1-204 Et FSO₂Me 1-205 Et NH(CH₂)₂OMe SO₂Me 1-206 —i-Pr SO₂Me CF₃ 1-207 cPr SO₂MeCF₃ 1-208 CF₃ O(CH₂)₂OMe F 1-209 CF₃ O(CH₂)₃OMe F 1-210 CF₃ OCH₂CONMe₂ F1-211 CF₃ [1,4]dioxan-2-yl- F methoxy 1-212 CF₃ O(CH₂)₂OMe Cl 1-213 CF₃O(CH₂)₃OMe Cl 1-214 CF₃ OCH₂CONMe₂ Cl 1-215 CF₃ [1,4]dioxan-2-yl- Clmethoxy 1-216 CF₃ O(CH₂)₂OMe Br 1-217 CF₃ O(CH₂)₃OMe Br 1-218 CF₃OCH₂CONMe₂ Br 1-219 CF₃ [1,4]dioxan-2-yl- Br methoxy 1-220 CF₃O(CH₂)₂OMe I 1-221 CF₃ O(CH₂)₃OMe I 1-222 CF₃ OCH₂CONMe₂ I 1-223 CF₃[1,4]dioxan-2- I ylmethoxy 1-224 CF₃ F SO₂Me 1-225 CF₃ F SO₂Et 1-226 CF₃O(CH₂)₂OMe SO₂Me 1-227 CF₃ O(CH₂)₂OMe SO₂Et 1-228 CF₃ O(CH₂)₃OMe SO₂Me1-229 CF₃ O(CH₂)₃OMe SO₂Et 1-230 CF₃ OCH₂CONMe₂ SO₂Me 1-231 CF₃OCH₂CONMe₂ SO₂Et 1-232 CF₃ [1,4]dioxan-2- SO₂Me ylmethoxy 1-233 CF₃[1,4]dioxan-2- SO₂Et ylmethoxy 1-234 F SMe CF₃ 1-235 F SOMe CF₃ 1-236 ClMe Cl 1-237 Cl OCH₂CHCH₂ Cl 1-238 Cl OCH₂CHF₂ Cl 1-239 Cl O(CH₂)₂OMe Cl1-240 Cl OCH₂CONMe₂ Cl 1-241 Cl O(CH₂)-5-pyrrolidin- Cl 2-one 1-242 ClSMe Cl 1-243 Cl SOMe Cl 1-244 Cl SO₂Me Cl 1-245 Cl F SMe 1-246 Cl ClSO₂Me 1-247 Cl CO₂Me SO₂Me 1-248 Cl CONMe₂ SO₂Me 1-249 Cl CONMe(OMe)SO₂Me 1-250 Cl CH₂OMe SO₂Me 1-251 Cl CH₂OMe SO₂Et 1-252 Cl CH₂OEt SO₂Me1-253 Cl CH₂OEt SO₂Et 1-254 Cl CH₂OCH₂CHF₂ SO₂Me 1-255 Cl CH₂OCH₂CF₃SO₂Me 1-256 Cl CH₂OCH₂CF₃ SO₂Et 1-257 Cl CH₂OCH₂CF₂CHF₂ SO₂Me 1-258 ClCH₂OcPentyl SO₂Me 1-259 Cl CH₂PO(OMe)₂ SO₂Me 1-260 Cl 4,5-dihydro-1,2-SMe oxazol-3-yl 1-261 Cl 4,5-dihydro-1,2- SO₂Me oxazol-3-yl 1-262 Cl4,5-dihydro-1,2- SO₂Et oxazol-3-yl 1-263 Cl 5-cyanomethyl-4,5- SO₂Medihydro-1,2-oxazol-3-yl 1-264 Cl 5-cyanomethyl-4,5- SO₂Etdihydro-1,2-oxazol-3-yl 1-265 Cl 5-(methoxymethyl)- SO₂Et4,5-dihydro-1,2- oxazol-3-yl 1-266 Cl 5-(methoxymethyl)- SO₂Et5-methyl-4,5-dihydro- 1,2-oxazol-3-yl 1-267 Cl CH₂O- SO₂Metetrahydrofuran-3-yl 1-268 Cl CH₂O- SO₂Et tetrahydrofuran-3-yl 1-269 ClCH₂OCH₂- SO₂Me tetrahydrofuran-2-yl 1-270 Cl CH₂OCH₂- SO₂Ettetrahydrofuran-2-yl 1-271 Cl CH₂OCH₂- SO₂Me tetrahydrofuran-3-yl 1-272Cl CH₂OCH₂- SO₂Et tetrahydrofuran-3-yl 1-273 Cl OMe SO₂Me 1-274 Cl OMeSO₂Et 1-275 Cl OEt SO₂Me 1-276 Cl OEt SO₂Et 1-277 Cl O—i-Pr SO₂Me 1-278Cl O—i-Pr SO₂Et 1-279 Cl O(CH₂)₂OMe SO₂Me 1-280 Cl O(CH₂)₄OMe SO₂Me1-281 Cl O(CH₂)₄OMe SO₂Et 1-282 Cl O(CH₂)₃OMe SO₂Me 1-283 Cl O(CH₂)₃OMeSO₂Et 1-284 Cl O(CH₂)₂OMe SO₂Me 1-285 Cl O(CH₂)₂OMe SO₂Et 1-286 Cl[1,4]dioxan-2- SO₂Me ylmethoxy 1-287 Cl [1,4]dioxan-2- SO₂Et ylmethoxy1-288 Cl OCH₂(CO)NMe₂ SO₂Me 1-289 Cl OCH₂(CO)NMe₂ SO₂Et 1-290 Cl SMeSO₂Me 1-291 Cl SOMe SO₂Me 1-292 Br OMe Br 1-293 Br O(CH₂)₂OMe Br 1-294Br O(CH₂)₂OMe SO₂Me 1-295 Br O(CH₂)₂OMe SO₂Et 1-296 Br O(CH₂)₃OMe SO₂Me1-297 Br O(CH₂)₃OMe SO₂Et 1-298 Br O(CH₂)₄OMe SO₂Me 1-299 Br O(CH₂)₄OMeSO₂Et 1-300 Br [1,4]dioxan-2- SO₂Me ylmethoxy 1-301 Br [1,4]dioxan-2-SO₂Et ylmethoxy 1-302 I O(CH₂)₂OMe SO₂Me 1-303 I O(CH₂)₂OMe SO₂Et 1-304I O(CH₂)₃OMe SO₂Me 1-305 I O(CH₂)₃OMe SO₂Et 1-306 I O(CH₂)₄OMe SO₂Me1-307 I O(CH₂)₄OMe SO₂Et 1-308 I [1,4]dioxan-2- SO₂Me ylmethoxy 1-309 I[1,4]dioxan-2- SO₂Et ylmethoxy 1-310 OMe SMe CF₃ 1-311 OMe SOMe CF₃1-312 OMe SO₂Me CF₃ 1-313 OMe SOEt CF₃ 1-314 OMe SO₂Et CF₃ 1-315 OMeS(CH₂)₂OMe CF₃ 1-316 OMe SO(CH₂)₂OMe CF₃ 1-317 OMe SO₂(CH₂)₂OMe CF₃1-318 OMe SMe Cl 1-319 OMe SOMe Cl 1-320 OMe SO₂Me Cl 1-321 OMe SEt Cl1-322 OMe SOEt Cl 1-323 OMe SO₂Et Cl 1-324 OMe S(CH₂)₂OMe Cl 1-325 OMeSO(CH₂)₂OMe Cl 1-326 OMe SO₂(CH₂)₂OMe Cl 1-327 OCH₂c-Pr SMe CF₃ 1-328OCH₂c-Pr SOMe CF₃ 1-329 OCH₂c-Pr SO₂Me CF₃ 1-330 OCH₂c-Pr SEt CF₃ 1-331OCH₂c-Pr SOEt CF₃ 1-332 OCH₂c-Pr SO₂Et CF₃ 1-333 OCH₂c-Pr S(CH₂)₂OMe CF₃1-334 OCH₂c-Pr SO(CH₂)₂OMe CF₃ 1-335 OCH₂c-Pr SO₂(CH₂)₂OMe CF₃ 1-336OCH₂c-Pr SMe Cl 1-337 OCH₂c-Pr SOMe Cl 1-338 OCH₂c-Pr SO₂Me Cl 1-339OCH₂c-Pr SEt Cl 1-340 OCH₂c-Pr SOEt Cl 1-341 OCH₂c-Pr SO₂Et Cl 1-342OCH₂c-Pr S(CH₂)₂OMe Cl 1-343 OCH₂c-Pr SO(CH₂)₂OMe Cl 1-344 OCH₂c-PrSO₂(CH₂)₂OMe Cl 1-345 OCH₂c-Pr SMe SO₂Me 1-346 OCH₂c-Pr SOMe SO₂Me 1-347OCH₂c-Pr SO₂Me SO₂Me 1-348 OCH₂c-Pr SEt SO₂Me 1-349 OCH₂c-Pr SOEt SO₂Me1-350 OCH₂c-Pr SO₂Et SO₂Me 1-351 OCH₂c-Pr S(CH₂)₂OMe SO₂Me 1-352OCH₂c-Pr SO(CH₂)₂OMe SO₂Me 1-353 OCH₂c-Pr SO₂(CH₂)₂OMe SO₂Me 1-354 SO₂MeF CF₃ 1-355 SO₂Me NH₂ CF₃ 1-356 SO₂Me NHEt Cl 1-357 SMe SEt F 1-358 SMeSMe F 1-359 SMe SMe CF₃ 1-360 SMe SOMe CF₃ 1-361 SMe SO₂Me CF₃ 1-362 SMeSMe Cl 1-363 SMe SMe Br 1-364 Cl Ac CF₃ 1-365 Cl Ac SO₂Me 1-366 ClC(O)cPr CF₃ 1-367 Cl C(O)cPr SO₂Me 1-368 Cl CH₂SMe CF₃ 1-369 ClCH₂S(O)Me CF₃ 1-370 Cl CH₂SO₂Me CF₃ 1-371 Cl CH₂SMe SO₂Me 1-372 ClCH₂S(O)Me SO₂Me 1-373 Cl CH₂SO₂Me SO₂Me 1-374 Cl CH═NOMe CF₃ 1-375 ClCH═NOMe SO₂Me 1-376 Cl 4,5-dihydro-1,2- CF₃ oxazol-5-yl, 1-377 Cl4,5-dihydro-1,2- SO₂Me oxazol-5-yl, 1-378 Cl 3-methyl-4,5-dihydro- CF₃1,2-oxazol-5-yl 1-379 Cl 3-methyl-4,5-dihydro- SO₂Me 1,2-oxazol-5-yl1-380 Cl vinyl CF₃ 1-381 Cl vinyl SO₂Me 1-382 Cl CO₂Me CF₃ 1-383 ClCO₂Me SO₂Me 1-384 Cl SMe CF₃ 1-385 Cl S(O)Me CF₃ 1-386 Cl SO₂Me CF₃1-387 Cl SO₂Me SO₂Me 1-388 Cl SMe Me 1-389 Cl SOMe Me 1-390 Cl SO₂Me Me1-391 Cl 1H-1,2,4-triazol-1-yl CF₃ 1-392 Cl 1H-1,2,3-triazol-1-yl CF₃1-393 Cl 2H-1,2,3-triazol-2-yl CF₃ 1-394 Cl 1H-pyrazol-1-yl CF₃ 1-395 Cl1H-4-chloropyrazol-1-yl CF₃ 1-396 Cl 1H-3-bromopyrazol- CF₃ 1-yl 1-397Cl 1H-4-trifluoromethyl- CF₃ pyrazol-1-yl 1-398 Cl pyrolidin-2-on-1-ylCF₃ 1-399 Cl morpholin-3-on-4-yl CF₃ 1-400 Cl 1,2-thiazolidine-1,1- CF₃dioxid-2-yl 1-401 Br 1H-1,2,4-triazol-1-yl CF₃ 1-402 Br1H-1,2,3-triazol-1-yl CF₃ 1-403 Br 2H-1,2,3-triazol-2-yl CF₃ 1-404 Br1H-pyrazol-1-yl CF₃ 1-405 Br 1H-4-chloropyrazol-1-yl CF₃ 1-406 Br1H-3-bromopyrazol- CF₃ 1-yl 1-407 Br 1H-4-trifluoromethyl- CF₃pyrazol-1-yl 1-408 Br pyrolidin-2-on-1-yl CF₃ 1-409 Brmorpholin-3-on-4-yl CF₃ 1-410 Br 1,2-thiazolidine-1,1- CF₃ dioxid-2-yl1-411 CH₂OMe 1H-1,2,4-triazol-1-yl CF₃ 1-412 CH₂OMe1H-1,2,3-triazol-1-yl CF₃ 1-413 CH₂OMe 2H-1,2,3-triazol-2-yl CF₃ 1-414CF₃ OCH₂CH₂F CF₃ 1-415 CF₃ OMe CF₃ 1-416 CF₃ SMe CF₃ 1-417 CF₃ SOMe CF₃1-418 CF₃ SO₂Me CF₃ 1-419 CF₃ 1H-pyrazol-1-yl CF₃ 1-420 Me SMe Et 1-421Me SOMe Et 1-422 Me SO₂Me Et 1-423 Me 1H-pyrazol-1-yl Et 1-424 MeOCH₂CH₂F Et 1-425 Me OMe Et 1-426 Me Ac CF₃ 1-427 Me Ac SO₂Me 1-428 MeC(O)cPr CF₃ 1-429 Me C(O)cPr SO₂Me 1-430 Me CH₂SMe CF₃ 1-431 MeCH₂S(O)Me CF₃ 1-432 Me CH₂SO₂Me CF₃ 1-433 Me CH₂SMe SO₂Me 1-434 MeCH₂S(O)Me SO₂Me 1-435 Me CH₂SO₂Me SO₂Me 1-436 Me CH═NOMe CF₃ 1-437 MeCH═NOMe SO₂Me 1-438 Me 4,5-dihydro-1,2- CF₃ oxazol-5-yl, 1-439 Me4,5-dihydro-1,2- SO₂Me oxazol-5-yl, 1-440 Me 3-methyl-4,5-dihydro- CF₃1,2-oxazol-5-yl 1-441 Me 3-methyl-4,5-dihydro- SO₂Me 1,2-oxazol-5-yl1-442 Me vinyl CF₃ 1-443 Me vinyl SO₂Me 1-444 Me CO₂Me CF₃ 1-445 MeCO₂Me SO₂Me 1-446 Cl SMe CF₃ 1-447 Cl SOMe CF₃ 1-448 Cl SO₂Me CF₃ 1-449Et SEt CF₃ 1-450 Et SOEt CF₃ 1-451 Et SO₂Et CF₃

TABLE 2 Compounds of the general formula (I) according to the invention,where A is A1, B is N, R⁶ is ethyl, R is CH(Me)OCO₂Et, W is CY and V ishydrogen. Table 2 comprises 451 compounds (2-1 to 2-451) in which X, Yand Z are defined in Table 1.

TABLE 3 Compounds of the general formula (I) according to the invention,where A is A1, B is N, R⁶ is methyl, R is CH(Me)OCO₂Me, W is CY and V ishydrogen. Table 3 comprises 451 compounds (3-1 to 3-451) in which X, Yand Z are defined in Table 1.

TABLE 4 Compounds of the general formula (I) according to the invention,where A is A1, B is N, R6 is ethyl, R is CH(Me)OCO₂Me, W is CY and V ishydrogen. Table 4 comprises 451 compounds (4-1 to 4-451) in which X, Yand Z are defined in Table 1.

TABLE 5 Compounds of the general formula (I) according to the invention,where A is A1, B is N, R6 is methyl, R is CH(Me)OCO₂-c-hexyl, W is CYand V is hydrogen. Table 5 comprises 451 compounds (5-1 to 5-451) inwhich X, Y and Z are defined in Table 1.

TABLE 6 Compounds of the general formula (I) according to the invention,where A is A1, B is N, R6 is ethyl, R is CH(Me)OCO₂-c-hexyl, W is CY andV is hydrogen. Table 6 comprises 451 compounds (6-1 to 6-451) in whichX, Y and Z are defined in Table 1.

TABLE 7 Compounds of the general formula (I) according to the invention,where A is A1, B is CH, R⁶ is methyl, R is CH(Me)OCO₂Et, W is CY and Vis hydrogen. Table 7 comprises 451 compounds (7-1 to 7-451) in which X,Y and Z are defined in Table 1.

TABLE 8 Compounds of the general formula (I) according to the invention,where A is A1, B is CH, R⁶ is methyl, R is CH(Me)OCO₂Me, W is CY and Vis hydrogen. Table 8 comprises 451 compounds (8-1 to 8-451) in which X,Y and Z are defined in Table 1.

TABLE 9 Compounds of the general formula (I) according to the invention,where A is A1, B is CH, R⁶ is methyl, R is CH(Me)OCO₂-c-hexyl, W is CYand V is hydrogen. Table 9 comprises 451 compounds (9-1 to 9-451) inwhich X, Y and Z are defined in Table 1.

TABLE 10 Compounds of the general formula (I) according to theinvention, where A is A2, B is N, R⁶ is methyl, R is CH(Me)OCO₂Et, W isCY and V is hydrogen. Table 10 comprises 451 compounds (10-1 to 10-451)in which X, Y and Z are defined in Table 1.

TABLE 11 Compounds of the general formula (I) according to theinvention, where A is A2, B is N, R⁶ is ethyl, R is CH(Me)OCO₂Et, W isCY and V is hydrogen. Table 11 comprises 451 compounds (11-1 to 11-451)in which X, Y and Z are defined in Table 1.

TABLE 12 Compounds of the general formula (I) according to theinvention, where A is A2, B is N, R⁶ is methyl, R is CH(Me)OCO₂Me, W isCY and V is hydrogen. Table 12 comprises 451 compounds (12-1 to 12-451)in which X, Y and Z are defined in Table 1.

TABLE 13 Compounds of the general formula (I) according to theinvention, where A is A2, B is N, R⁶ is ethyl, R is CH(Me)OCO₂Me, W isCY and V is hydrogen. Table 13 comprises 451 compounds (13-1 to 13-451)in which X, Y and Z are defined in Table 1.

TABLE 14 Compounds of the general formula (I) according to theinvention, where A is A2, B is N, R⁶ is methyl, R is CH(Me)OCO₂-c-hexyl,W is CY and V is hydrogen. Table 14 comprises 451 compounds (14-1 to14-451) in which X, Y and Z are defined in Table 1.

TABLE 15 Compounds of the general formula (I) according to theinvention, where A is A2, B is N, R⁶ is ethyl, R is CH(Me)OCO₂-c-hexyl,W is CY and V is hydrogen. Table 15 comprises 451 compounds (15-1 to15-451) in which X, Y and Z are defined in Table 1.

TABLE 16 Compounds of the general formula (I) according to theinvention, where A is A2, B is CH, R⁶ is methyl, R is CH(Me)OCO₂Et, W isCY and V is hydrogen. Table 16 comprises 451 compounds (16-1 to 16-451)in which X, Y and Z are defined in Table 1.

TABLE 17 Compounds of the general formula (I) according to theinvention, where A is A2, B is CH, R⁶ is methyl, R is CH(Me)OCO₂Me, W isCY and V is hydrogen. Table 17 comprises 451 compounds (17-1 to 17-451)in which X, Y and Z are defined in Table 1.

TABLE 18 Compounds of the general formula (I) according to theinvention, where A is A2, B is CH, R⁶ is methyl, R isCH(Me)OCO₂-c-hexyl, W is CY and V is hydrogen. Table 18 comprises 451compounds (18-1 to 18-451) in which X, Y and Z are defined in Table 1.

TABLE 19 Compounds of the general formula (I) according to theinvention, where A is A3, B is N, R⁶ is methyl, R is CH(Me)OCO₂Et, W isCY and V is hydrogen. Table 19 comprises 451 compounds (19-1 to 19-451)in which X, Y and Z are defined in Table 1.

TABLE 20 Compounds of the general formula (I) according to theinvention, where A is A3, B is N, R⁶ is ethyl, R is CH(Me)OCO₂Et, W isCY and V is hydrogen. Table 20 comprises 451 compounds (20-1 to 20-451)in which X, Y and Z are defined in Table 1.

TABLE 21 Compounds of the general formula (I) according to theinvention, where A is A3, B is N, R⁶ is methyl, R is CH(Me)OCO₂Me, W isCY and V is hydrogen. Table 20 comprises 451 compounds (20-1 to 20-451)in which X, Y and Z are defined in Table 1.

TABLE 22 Compounds of the general formula (I) according to theinvention, where A is A3, B is N, R⁶ is ethyl, R is CH(Me)OCO₂Me, W isCY and V is hydrogen. Table 22 comprises 451 compounds (22-1 to 22-451)in which X, Y and Z are defined in Table 1.

TABLE 23 Compounds of the general formula (I) according to theinvention, where A is A3, B is N, R⁶ is methyl, R is CH(Me)OCO₂-c-hexyl,W is CY and V is hydrogen. Table 23 comprises 451 compounds (23-1 to23-451) in which X, Y and Z are defined in Table 1.

TABLE 24 Compounds of the general formula (I) according to theinvention, where A is A3, B is N, R⁶ is ethyl, R is CH(Me)OCO₂-c-hexyl,W is CY and V is hydrogen. Table 24 comprises 451 compounds (24-1 to24-451) in which X, Y and Z are defined in Table 1.

TABLE 25 Compounds of the general formula (I) according to theinvention, where A is A3, B is CH, R⁶ is methyl, R is CH(Me)OCO₂Et, W isCY and V is hydrogen. Table 25 comprises 451 compounds (25-1 to 25-451)in which X, Y and Z are defined in Table 1.

TABLE 26 Compounds of the general formula (I) according to theinvention, where A is A3, B is N, R⁶ is methyl, R is CH(Me)OCO₂Me, W isCY and V is hydrogen. Table 26 comprises 451 compounds (26-1 to 26-451)in which X, Y and Z are defined in Table 1.

TABLE 27 Compounds of the general formula (I) according to theinvention, where A is A3, B is CH, R⁶ is methyl, R isCH(Me)OCO₂-c-hexyl, W is CY and V is hydrogen. Table 27 comprises 451compounds (27-1 to 27-451) in which X, Y and Z are defined in Table 1.

TABLE 28 Compounds of the general formula (I) according to theinvention, where A is A4, B is N, R⁶ is methyl, R is CH(Me)OCO₂Et, W isCY and V is hydrogen. Table 28 comprises 451 compounds (28-1 to 28-451)in which X, Y and Z are defined in Table 1.

TABLE 29 Compounds of the general formula (I) according to theinvention, where A is A4, B is N, R⁶ is ethyl, R is CH(Me)OCO₂Et, W isCY and V is hydrogen. Table 29 comprises 451 compounds (29-1 to 29-451)in which X, Y and Z are defined in Table 1.

TABLE 30 Compounds of the general formula (I) according to theinvention, where A is A4, B is N, R⁶ is methyl, R is CH(Me)OCO₂Me, W isCY and V is hydrogen. Table 30 comprises 451 compounds (30-1 to 30-451)in which X, Y and Z are defined in Table 1.

TABLE 31 Compounds of the general formula (I) according to theinvention, where A is A4, B is N, R⁶ is ethyl, R is CH(Me)OCO₂Me, W isCY and V is hydrogen. Table 31 comprises 451 compounds (31-1 to 31-451)in which X, Y and Z are defined in Table 1.

TABLE 32 Compounds of the general formula (I) according to theinvention, where A is A4, B is N, R⁶ is methyl, R is CH(Me)OCO₂-c-hexyl,W is CY and V is hydrogen. Table 32 comprises 451 compounds (32-1 to32-451) in which X, Y and Z are defined in Table 1.

TABLE 33 Compounds of the general formula (I) according to theinvention, where A is A4, B is N, R⁶ is ethyl, R is CH(Me)OCO₂-c-hexyl,W is CY and V is hydrogen. Table 33 comprises 451 compounds (33-1 to33-451) in which X, Y and Z are defined in Table 1.

TABLE 34 Compounds of the general formula (I) according to theinvention, where A is A4, B is CH, R⁶ is methyl, R is CH(Me)OCO₂Et, W isCY and V is hydrogen. Table 34 comprises 451 compounds (34-1 to 34-451)in which X, Y and Z are defined in Table 1.

TABLE 35 Compounds of the general formula (I) according to theinvention, where A is A4, B is CH, R⁶ is methyl, R is CH(Me)OCO₂Me, W isCY and V is hydrogen. Table 35 comprises 451 compounds (35-1 to 35-451)in which X, Y and Z are defined in Table 1.

TABLE 36 Compounds of the general formula (I) according to theinvention, where A is A4, B is CH, R⁶ is methyl, R isCH(Me)OCO₂-c-hexyl, W is CY and V is hydrogen. Table 36 comprises 451compounds (36-1 to 36-451) in which X, Y and Z are defined in Table 1.

TABLE 37 Compounds of the general formula (I) according to theinvention, where A is A1, B is N, W is CY and V is hydrogen and R, R⁶, Xand Z have the definitions specified in Table 37

Physical data No. X Z R⁶ R (¹H NMR, DMSO-d₆, 400 MHz) 10-1  Cl CF₃ MeCH(Me)OCO₂Et 10-2  Cl CF₃ Me CH(Me)OCO₂Me 10-3  Cl CF₃ MeCH(Me)OCO₂-c-hexyl 10-4  Cl CF₃ Et CH(Me)OCO₂Et 10-5  Cl CF₃ EtCH(Me)OCO₂Me 10-6  Cl CF₃ Et CH(Me)OCO₂-c-hexyl 10-7  Br CF₃ MeCH(Me)OCO₂Et 10-8  Br CF₃ Me CH(Me)OCO₂Me 10-9  Br CF₃ MeCH(Me)OCO₂-c-hexyl 10-10 Br CF₃ Et CH(Me)OCO₂Et 10-11 Br CF₃ EtCH(Me)OCO₂Me 10-12 Br CF₃ Et CH(Me)OCO₂-c-hexyl 10-13 Me CF₃ MeCH(Me)OCO₂Et 10-14 Me CF₃ Me CH(Me)OCO₂Me 10-15 Me CF₃ MeCH(Me)OCO₂-c-hexyl 10-16 Me CF₃ Et CH(Me)OCO₂Et 10-17 Me CF₃ EtCH(Me)OCO₂Me 10-18 Me CF₃ Et CH(Me)OCO₂-c-hexyl 10-19 CH₂OMe CF₃ MeCH(Me)OCO₂Et 10-20 CH₂OMe CF₃ Me CH(Me)OCO₂Me 10-21 CH₂OMe CF₃ MeCH(Me)OCO₂-c-hexyl 10-22 CH₂OMe CF₃ Et CH(Me)OCO₂Et 10-23 CH₂OMe CF₃ EtCH(Me)OCO₂Me 10-24 CH₂OMe CF₃ Et CH(Me)OCO₂-c-hexyl 10-25 CH₂OCH₂CH₂OMeCF₃ Me CH(Me)OCO₂Et 10-26 CH₂OCH₂CH₂OMe CF₃ Me CH(Me)OCO₂Me 10-27CH₂OCH₂CH₂OMe CF₃ Me CH(Me)OCO₂-c-hexyl 10-28 CH₂OCH₂CH₂OMe CF₃ EtCH(Me)OCO₂Et 10-29 CH₂OCH₂CH₂OMe CF₃ Et CH(Me)OCO₂Me 10-30 CH₂OCH₂CH₂OMeCF₃ Et CH(Me)OCO₂-c-hexyl

TABLE 38 Compounds of the general formula (I) according to theinvention, where A is A2, B is N, W is CY and V is hydrogen. Table 38comprises 30 compounds (38-1 to 38-30) in which R, R⁶, X and Z are asdefined in Table 37.

TABLE 39 Compounds of the general formula (I) according to theinvention, where A is A3, B is N, W is CY and V is hydrogen. Table 39comprises 30 compounds (39-1 to 39-30) in which R, R⁶, X and Z are asdefined in Table 37.

TABLE 40 Compounds of the general formula (I) according to theinvention, where A is A4, B is N, W is CY and V is hydrogen. Table 40comprises 30 compounds (40-1 to 40-30) in which R, R⁶, X and Z are asdefined in Table 37.

The abbreviations used mean:

Et = ethyl Me = methyl n-Pr = n-propyl i-Pr = isopropyl c-Pr =cyclopropyl Ph = phenyl Bn = benzyl Bu = butyl c = cyclo

B. FORMULATION EXAMPLES

-   -   a) A dusting product is obtained by mixing 10 parts by weight of        a compound of the formula (I) and 90 parts by weight of talc as        inert substance and comminuting the mixture in a hammer mill.    -   b) A wettable powder which is readily dispersible in water is        obtained by mixing 25 parts by weight of a compound of the        formula (I), 64 parts by weight of kaolin-containing quartz as        inert substance, 10 parts by weight of potassium lignosulfonate        and 1 part by weight of sodium oleoylmethyltaurate as wetting        agent and dispersant, and grinding the mixture in a pinned-disk        mill.    -   c) A readily water-dispersible dispersion concentrate is        obtained by mixing 20 parts by weight of a compound of the        formula (I) with 6 parts by weight of alkylphenol polyglycol        ether (®Triton X 207), 3 parts by weight of isotridecanol        polyglycol ether (8 EO) and 71 parts by weight of paraffinic        mineral oil (boiling range for example about 255 to above 277°        C.) and grinding the mixture in a ball mill to a fineness of        below 5 microns.    -   d) An emulsifiable concentrate is obtained from 15 parts by        weight of a compound of the formula (I), 75 parts by weight of        cyclohexanone as solvent and 10 parts by weight of oxyethylated        nonylphenol as emulsifier.    -   e) Water-dispersible granules are obtained by mixing    -   75 parts by weight of a compound of the formula (I) and/or salts        thereof,    -   10 parts by weight of calcium lignosulfonate,    -   5 parts by weight of sodium lauryl sulfate,    -   3 parts by weight of polyvinyl alcohol and    -   7 parts by weight of kaolin,    -   grinding the mixture in a pinned-disk mill, and granulating the        powder in a fluidized bed by spray application of water as a        granulating liquid.

f) Water-dispersible granules are also obtained by homogenizing andprecomminuting, in a colloid mill,

-   -   25 parts by weight of a compound of the formula (I),    -   5 parts by weight of sodium        2,2′-dinaphthylmethane-6,6′-disulfonate    -   2 parts by weight of sodium oleoylmethyltaurate,    -   1 part by weight of polyvinyl alcohol    -   17 parts by weight of calcium carbonate and    -   50 parts by weight of water,    -   then grinding the mixture in a bead mill and atomizing and        drying the resulting suspension in a spray tower by means of a        one-phase nozzle.

C. Biological examples

1. Pre-Emergence Herbicidal Action Against Harmful Plants

Seeds of monocotyledonous and dicotyledonous weed plants and crop plantsare laid out in wood-fiber pots in sandy loam and covered with soil. Thecompounds of the invention, formulated in the form of wettable powders(WP) or as emulsion concentrates (EC), are then applied to the surfaceof the covering soil in the form of an aqueous suspension or emulsion ata water application rate equating to 600 to 800 I/ha, with addition of0.2% wetting agent. After the treatment, the pots are placed in agreenhouse and kept under good growth conditions for the trial plants.The damage to the test plants is scored visually after a test period of3 weeks by comparison with untreated controls (herbicidal activity inpercent (%): 100% activity=the plants have died, 0% activity=likecontrol plants). Here, for example, the compounds Nos. 1-384, 1-390,3-384, 5-384, 19-384, 9-390, 21-384, 23-384 and 28-390, at anapplication rate of 320 g/ha, each show an activity of at least 80%against Stellaria media and Amaranthus retroflexus.

2. Post-Emergence Herbicidal Action Against Harmful Plants

Seeds of monocotyledonous and dicotyledonous weed and crop plants arelaid out in sandy loam soil in wood-fiber pots, covered with soil andcultivated in a greenhouse under good growth conditions. 2 to 3 weeksafter sowing, the test plants are treated at the one-leaf stage. Thecompounds of the invention, formulated in the form of wettable powders(WP) or as emulsion concentrates (EC), are then sprayed onto the greenparts of the plants in the form of an aqueous suspension or emulsion ata water application rate equating to 600 to 800 I/ha, with addition of0.2% wetting agent. After the test plants have been left to stand in thegreenhouse under optimal growth conditions for about 3 weeks, the actionof the preparations is assessed visually in comparison to untreatedcontrols (herbicidal action in percent (%): 100% activity=the plantshave died, 0% activity=like control plants). Here, for example, thecompounds Nos. 1-384, 1-390, 3-384, 5-384, 19-384, 9-390, 21-384,23-384, 28-390 and 32-384, at an application rate of 80 g/ha, each showan activity of at least 80% against Stellaria media and Veronicapersica.

3. Comparative Experiment in Pre-Emergence

For comparative purposes, the herbicidal activity of some compoundsaccording to the invention and the most structurally similar compoundsknown from the prior art were tested.

Herbicidal activity Compound Dosage [g/ha] against POLCO No. 1-390,inventive 320 100% No. 4-634, from WO 320 70% 2012/028579 No. 19-390,inventive 320 100% No. 4-634, from WO 320 70% 2012/028579 No. 28-390,inventive 320 90% No. 4-634, from WO 320 70% 2012/028579 No. 1-390,inventive 320 100% No. 3-040, from WO 320 70% 2014/126070 No. 28-390,inventive 320 90% No. 3-040, from WO 320 70% 2014/126070 No. 21-384,inventive 320 100% No. 4-638, from WO 320 50% 2012/028579 No. 23-384,inventive 320 90% No. 4-638, from WO 320 50% 2012/028579 No. 32-384,inventive 320 70% No. 4-638, from WO 320 50% 2012/028579

The experiments show, by way of example, the superior herbicidalactivity of the compounds according to the invention on the harmfulplant Polygonum convolvulus (POLCO).

1. An N-(tetrazol-5-yl)- and N-(triazol-5-yl)arylcarboxamide derivativeof the formula (I)

where the symbols and indices are each defined as follows: W is N or CY,X and Z are each independently hydrogen, nitro, halogen, cyano, formyl,thiocyanato, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl,(C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-haloalkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-halocycloalkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, (C₃-C₆)-halocycloalkyl-(C₁-C₆)-alkyl,COR¹, OR¹, OCOR¹, OSO₂R², S(O)_(n)R², SO₂OR¹, SO₂N(R¹)₂, NR¹SO₂R²,NR¹COR¹, (C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹,(C₁-C₆)-alkyl-OCOR¹, (C₁-C₆)-alkyl-OSO₂R², (C₁-C₆)-alkyl-CO₂R¹,(C₁-C₆)-alkyl-SO₂OR¹, (C₁-C₆)-alkyl-CON(R¹)₂, (C₁-C₆)-alkyl-SO₂N(R¹)₂,(C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R², NR¹R², P(O)(OR⁵)₂, orheteroaryl, heterocyclyl or phenyl, each substituted by s radicals fromthe group of methyl, ethyl, methoxy, nitro, trifluoromethyl and halogen,Y is hydrogen, nitro, halogen, cyano, thiocyanato, (C₁-C₆)-alkyl,halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl,(C₂-C₆)-alkynyl, halo-(C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkenyl, halo-(C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,COR¹, CO₂R¹, OCO₂R¹, NR¹CO₂R¹, C(O)N(R¹)₂, NR¹C(O)N(R¹)₂, OC(O)N(R¹)₂,C(O)N(R¹)OR¹, NR¹SO₂R², NR¹COR¹, OR¹, OSO₂R², S(O)_(n)R², SO₂OR¹,SO₂N(R¹)₂, (C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹,(C₁-C₆)-alkyl-OCOR¹, (C₁-C₆)-alkyl-OSO₂R², (C₁-C₆)-alkyl-CO₂R¹,(C₁-C₆)-alkyl-CN, (C₁-C₆)-alkyl-SO₂OR¹, (C₁-C₆)-alkyl-CON(R¹)₂,(C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R²,N(R¹)₂, P(O)(OR⁵)₂, CH₂P(O)(OR⁵)₂, CH═NOR¹, (C₁-C₆)-alkyl-CH═NOR¹,(C₁-C₆)-alkyl-O—N═C(R¹)₂, (C₁-C₆)-alkylphenyl, (C₁-C₆)-alkylheteroaryl,(C₁-C₆)-alkylheterocyclyl, phenyl, heteroaryl or heterocyclyl, where thelatter 6 radicals are each substituted by s radicals from the groupconsisting of halogen, nitro, cyano, (C₃-C₆)-cycloalkyl,S(O)_(n)-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy,(C₁-C₆)-alkoxy-(C₁-C4)-alkyl and cyanomethyl, and where heterocyclylbears n oxo groups, or Y and Z together with the two atoms to which theyare bonded form a 5-, 6- or 7-membered, unsaturated, partly saturated orsaturated ring which, as well as carbon atoms, in each case has snitrogen atoms, n oxygen atoms, n sulfur atoms and n S(O), S(O)₂,C═N—R¹⁰, C(OR¹¹)₂, C[—O—(CH₂)₂—O—] or C(O) elements as ring members,wherein the carbon atoms are substituted by s radicals from the groupconsisting of halogen, cyano, (C₁-C₆)-alkyl, (C₂-C₁₀)-alkenyl,(C₂-C₁₀)-alkynyl, (C₁-C₆)-haloalkyl, (C₁-C₆)-alkoxy, phenoxy,halo-(C₁-C₆)-alkoxy, (C₃-C8)-cycloalkyl, (C₂-C8)-alkoxyalkyl and phenyl,wherein the nitrogen atoms are substituted by n radicals from the groupconsisting of (C₁-C₆)-alkyl and phenyl, and in which the aforementionedphenyl radicals are substituted by s radicals from the group consistingof cyano, nitro, halogen, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl and(C₁-C₆)-alkoxy, V is hydrogen, nitro, halogen, cyano, (C₁-C4)-alkyl,(C₁-C4)-haloalkyl or OR¹, S(O)_(n)R², R¹ is hydrogen, (C₁-C₆)-alkyl,(C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl,(C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl, (C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkenyl, (C₃-C₆)-halocycloalkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, phenyl, phenyl-(C₁-C₆)-alkyl,heteroaryl, (C₁-C₆)-alkylheteroaryl, heterocyclyl,(C₁-C₆)-alkylheterocyclyl, (C₁-C₆)-alkyl-O-heteroaryl,(C₁-C₆)-alkyl-O-heterocyclyl, (C₁-C₆)-alkyl-NR³-heteroaryl or(C₁-C₆)-alkyl-NR³-heterocyclyl, where the 21 latter radicals aresubstituted by s radicals from the group consisting of cyano, halogen,nitro, thiocyanato, OR³, S(O)_(n)R⁴, N(R³)₂, NR³OR³, COR³, OCOR³, SCOR⁴,NR³COR³, NR³SO₂R⁴, CO₂R³, COSR⁴, CON(R³)₂ and(C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and where heterocyclyl bears noxo groups, R² is (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl,(C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl, (C₃-C₆)-halocycloalkyl,(C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, phenyl,phenyl-(C₁-C₆)-alkyl, heteroaryl, (C₁-C₆)-alkylheteroaryl, heterocyclyl,(C₁-C₆)-alkylheterocyclyl, (C₁-C₆)-alkyl-O-heteroaryl,(C₁-C₆)-alkyl-O-heterocyclyl, (C₁-C₆)-alkyl-NR³-heteroaryl,(C₁-C₆)-alkyl-NR³-heterocyclyl, where the 21 latter radicals aresubstituted by s radicals from the group consisting of cyano, halogen,nitro, thiocyanato, OR³, S(O)_(n)R⁴, N(R³)₂, NR³OR³, COR³, OCOR³, SCOR⁴,NR³COR³, NR³SO₂R⁴, CO₂R³, COSR⁴, CON(R³)₂ and(C₁-C4)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and where heterocyclyl bears noxo groups, R³ is hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,(C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl or (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,R⁴ is (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl or (C₂-C₆)-alkynyl,(C₃-C₆)-cycloalkyl or (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, R⁵ is(C₁-C₄)-alkyl, n is 0, 1 or 2, s is 0, 1, 2 or 3, A is an A1, A2, A3 orA4 radical

B is Nor CH, R is (C₁-C₆)-alkyl-OC(O)N(R³)₂ or (C₁-C₆)-alkyl-OC(O)OR¹²,R⁶ is (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₂-C₆)-alkynyl, where these6 aforementioned radicals are each substituted by s radicals from thegroup consisting of nitro, cyano, SiR⁹ ₃, PO(OR⁹)₃,S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy, N(R⁷)₂,COR⁷, CO₂R⁷, OCOR⁷, OCO₂R⁷, NR⁷COR⁷, NR⁷SO₂R⁸, (C₃-C₆)-cycloalkyl,heteroaryl, heterocyclyl, phenyl, D-heteroaryl, D-heterocyclyl, D-phenylor D-benzyl, and where the 7 latter radicals are substituted by sradicals from the group of methyl, ethyl, methoxy, trifluoromethyl andhalogen, and where heterocyclyl bears n oxo groups, or R⁶ is(C₃-C₇)-cycloalkyl, heteroaryl, heterocyclyl or phenyl, each substitutedby s radicals from the group consisting of halogen, nitro, cyano,(C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy and(C₁-C₆)-alkoxy-(C₁-C₄)-alkyl, R⁷ is hydrogen, (C₁-C₆)-alkyl,(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl or(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl or phenyl, R⁸ is (C₁-C₆)-alkyl,(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl or phenyl, R⁹ is (C₁-C)-alkyl, R¹⁰ is(C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy andhalo-(C₁-C₆)-alkoxy, R¹¹ is (C₁-C₆)-alkyl or halo-(C₁-C₆)-alkyl, R¹² is(C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl or (C₁-C₆)-cycloalkyl, s is 0, 1, 2 or3, n is 0, 1 or 2, D is O, S, or NR⁸.
 2. The N-(tetrazol-5-yl)- andN-(triazol-5-yl)arylcarboxamide derivative of the formula (I) as claimedin claim 1, where R⁶ is (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, where these 4 aforementioned radicalsare each substituted by s radicals from the group consisting ofS(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy, N(R⁷)₂,COR⁷, CO₂R⁷, OCOR⁷, OCO₂R⁷, NR⁷COR⁷, NR⁷SO₂R⁸, (C₃-C₆)-cycloalkyl,heteroaryl, heterocyclyl, phenyl, D-heteroaryl, D-heterocyclyl, D-phenylor D-benzyl, and where the 7 latter radicals are substituted by sradicals from the group of methyl, ethyl, methoxy, trifluoromethyl andhalogen, and where heterocyclyl bears n oxo groups, or R⁶ is(C₃-C₇)-cycloalkyl, heteroaryl, heterocyclyl or phenyl, each substitutedby s radicals from the group consisting of halogen, nitro, cyano,(C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy and(C₁-C₆)-alkoxy-(C₁-C₄)-alkyl.
 3. The N-(tetrazol-5-yl)- andN-(triazol-5-yl)arylcarboxamide derivative of the formula (I) as claimedin claim 1, where W is CY, X and Z are each independently hydrogen,halogen, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-halocycloalkyl, OR¹, S(O)_(n)R², SO₂N(R¹)₂,NR¹SO₂R², NR¹COR¹, (C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹, orheteroaryl, heterocyclyl or phenyl, each substituted by s radicals fromthe group of methyl, ethyl, methoxy, nitro, trifluoromethyl and halogen,Y is hydrogen, (C₂-C₆)-alkenyl, COR¹, CO₂R¹, OCO₂R¹, NR¹CO₂R¹,C(O)N(R¹)₂, NR¹C(O)N(R¹)₂, OC(O)N(R¹)₂, C(O)N(R¹)OR¹, NR¹SO₂R², NR¹COR¹,OR¹, S(O)_(n)R², SO₂N(R¹)₂, (C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹,(C₁-C₆)-alkyl-OCOR¹, (C₁-C₆)-alkyl-CO₂R¹, (C₁-C₆)-alkyl-CON(R¹)₂,(C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R²,N(R¹)₂, CH═NOR¹, (C₁-C₆)-alkyl-CH═NOR¹, (C₁-C₆)-alkylheteroaryl,(C₁-C₆)-alkylheterocyclyl, heteroaryl or heterocyclyl, where the 4latter radicals are each substituted by s radicals from the groupconsisting of halogen, nitro, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl, S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy,halo-(C₁-C₆)-alkoxy, (C₁-C₆)-alkoxy-(C₁-C4)-alkyl and cyanomethyl, andwhere heterocyclyl bears n oxo groups, V is hydrogen, Cl, OMe, methyl orethyl, R⁶ is methyl, ethyl, n-propyl.
 4. The N-(tetrazol-5-yl)- andN-(triazol-5-yl)arylcarboxamide derivative of the formula (I) as claimedin claim 1, where W is CY, X is F, Cl, Br, methyl, ethyl, cyclopropyl,trifluoromethyl, methoxy, methoxymethyl, methoxyethoxymethyl, SMe orSO₂Me, Z is hydrogen, F, Cl, Br, I, methyl, ethyl, trifluoromethyl,difluoromethyl, pentafluoroethyl, methyl sulfonyl or ethyl sulfonyl, Yis hydrogen, SMe, S(O)Me, SO₂Me, SEt, S(O)Et, SO₂Et, CH₂OMe, CH₂OEt,CH₂OCH₂CF₃, CH₂SMe, CH₂S(O)Me, CH₂SO₂Me, vinyl, C(O)Me, C(O)Et, C(O)cPr,CO₂Me, CHN═OMe, 4,5-dihydro-1,2-oxazol-3-yl,5-methyl-4,5-dihydro-1,2-oxazol-3-yl,5-methyl-4,5-dihydro-1,2-oxazol-3-yl,5-cyanomethyl-4,5-dihydro-1,2-oxazol-3-yl, 4,5-dihydro-1,2-oxazol-5-yl,3-methyl-4,5-dihydro-1,2-oxazol-5-yl, 1H-pyrazol-1-yl,1H-1,2,3-triazol-1-yl, 2H-1,2,3-triazol-2-yl, 1H-1,2,4-triazol-1-yl,pyrolidin-2-on-l-yl, morpholin-3-on-4-yl, OMe, OEt, O-n-Pr, OCH₂-c-Pr,OCH₂CH₂F; OCH₂CH₂OMe or OCH₂CH₂CH₂OMe, V is hydrogen, B is N, R isCH₂OCO₂Et, CH(CH₃)OCO₂Me, CH(CH₃)OCO₂Et, CH(CH₃)OCO₂-c-hexyl,CH(CH₃)OCO₂-i-Pr or CH(CH₃)OCO₂-t-Bu, R⁶ is methyl or ethyl.
 5. Aherbicidal composition comprising a herbicidally effective amount of atleast one N-(tetrazol-5-yl)- or N-(triazol-5-yl)arylcarboxamidederivative of the formula (I) as claimed in claim
 1. 6. The herbicidalcomposition as claimed in claim 5 in a mixture with one or moreformulation auxiliaries.
 7. The herbicidal composition as claimed inclaim 5, comprising at least one further pesticidally active substancefrom the group consisting of insecticides, acaricides, herbicides,fungicides, safeners, and growth regulators.
 8. The herbicidalcomposition as claimed in claim 7, comprising a safener.
 9. Theherbicidal composition as claimed in claim 5, comprising cyprosulfamide,cloquintocet-mexyl, mefenpyr-diethyl or isoxadifen-ethyl.
 10. Theherbicidal composition as claimed in claim 1, comprising a furtherherbicide.
 11. A method of controlling one or more unwanted plants,comprising applying an effective amount of at least one compound of theformula (I) as claimed in claim 1 or a herbicidal composition thereof tothe plants or to a site of unwanted vegetation.
 12. A product comprisinga compound of the formula (I) as claimed in claim 1 or a herbicidalcomposition thereof for controlling unwanted plants.
 13. The product asclaimed in claim 12, comprising using a compound of the formula (I) forcontrolling one or more unwanted plants in crops of one or more usefulplants.
 14. The product as claimed in claim 13, wherein the usefulplants are transgenic useful plants.